Sciencemadness Discussion Board

Phenyl-2-nitropropene reduction

aldol - 7-3-2005 at 22:56

I recently had a dream of reducingp2np to the amine with sn and hcl
Procedure went like this.
in a 2 litre beaker was 30 grams of recristlized p2np , 120 grams granulated tin with just enough water to cover contents.
A mechanical stirrer was fitted and the contents was heated to 50c
added dropwise was 200ml of 37% hcl over a period of 8 hours
the contents upon conpletion of the reduction had gone from a yellow p2np colour to to clear water
I then carefully basified water to ph13 which percipertated out tin hydroxide whitch i filtered out
I then had a yellow as water phase with a little bit of sodium cloride in it from reaction
Next i evaperated down the water to yeild a yellow product mixed with sodium cloride
When it was dry i added 250ml dry ethanol which dessolved the organic phase but not the nacl i then had a nice yellow alcohol phase
Dropwise i added conc h2so4 which percipertated out a very white powder
I then filtered to collect 26 grams of product wich i thought was amphetamine sulphate but was not did it go to the oxime or some other intermediate could somewone with more knowledge tan me help
I would be much apprecaited thank you:o

Edit by Chemoleo: Changed title, you can't assume everyone knows what p2np is.

[Edited on 8-3-2005 by chemoleo]

phenyl 2 nitro propene

aldol - 8-3-2005 at 12:45

thank chemolio for the change although if they don t no about p2np they proberly would not no anything about the conplex chemistry involving p2np :cool:

runlabrun - 8-3-2005 at 19:04

Its not that complex.... and p2np is not a correct chemical descriptor, just a clandestine chem acronym...
More likely that you have the oxime after this method, what was your reference? source of info....



aldol - 8-3-2005 at 20:04

HIGH RUN LAB RUN i had no referances to this method i new tin was selective towards nitro compounds so i worked out a method myself
not bad yeild pitty its not the goods
regards to phenyl 2 nitro propene any compound that can be rearanged into 4 or five compounds is not simple chemistry
if i had access to a mass spec i would have had it going a long time ago
if i new what the intermediate was i would no what to do with it regards
regards aldol

runlabrun - 9-3-2005 at 22:43

Rhodium backups have a nice page of this proceedure using easy materials..
im not going to post the method but look for it on one of the millions of backups online...
"Amphetamine from P2NP using Urushibara Nickel (NiCl2/Al) "



aldol - 10-3-2005 at 01:45

hi lab run lab
thanks for the info i have played with urishabara catylist
made from zinc i have not used aluminium to percipetate the nickel
I did not try the reduction using it
i thought there would be a problem scaling up
thinking about the 8 time molar excess of aluminium
where in my tin reduction i can scale up huge have tryed it 2kg no problem
has any one scaled the urishabara method if so i would like to here
from you, and can you reduce the oxime with urishabara and can anyone help with a good reduction for the oxime

the more the frustration the more the reward:o ALDOL


aldol - 10-3-2005 at 14:57

shorly someone has thoughts on this lots of lookers the method is so clean
and the workup is simple
posting a good method like this deseves a response
i have a method for p2np no glassware
just a coke bottle sit on shelf for 2 weeks
depending on weather volla i have seen
this done with cyclohexylamine as catylist but have not seen a method for ammonium acetate my method is billiant low key but am reluctant to post it wy post it when you get no responce
or is it all the people o n this site dreamers or studants anyone can put refs on about methods you can get anywhere but when it comes to the crunch studants and dreamers think they can help but cannot i have heeps of exsperiance with production of p2p and methylamine lots of other procedures but why should i share my exspeariances
not dreams

enima - 10-3-2005 at 15:34

Take a look at the Al/Hg reduction of nitrostyrenes on rhodiums website, p2np is reduced to amphetamine with a 83% yield. All you need is some foil and some mercury salt. (you can scale this reaction to some degree)

I'm personally don't like metal + hcl reductions they are very unreliable and yields are piss poor.


aldol - 10-3-2005 at 16:20

thanks anima have used hgsalts in reductive aminations bot i am trying to get away from nasty hg salts now i am using different precurses
have you done na metal in alcohol reduction of the oxime is it a good clean method i no vogul uses it but i would like to no

Darkfire - 10-3-2005 at 17:58

You can get away from the Hg salts and still do a Hg/Al reduction by sticking to using elemental mercury, which is significantly less toxic. Measure out your mercury in the reaction flask, then add the proportional amount of HNO3 and wait for the mercury to be turned to its salt. This save you from storeing, measuring, and messing around with the salt until its in your reaction vessel ready to go.

enima - 10-3-2005 at 19:08

yea, I understand why you'd want to avoid mercury salts. I'm so paranoid that I go through 4-5 pairs of gloves from removing the salt from its container to putting it back in the container.

Anyway, you might have an oxime, I know that Lead in Acetic acid reduced nitroalkenes to oximes. You could try the reduction with zinc. Mix the nitropropene with the zinc and slowly add it to an HCL ethanol solution. I'm not sure on the precise proceedure. But I attempted this a long time ago (with 3-methoxy-4-hydroxynitrostyrene) and I did get a product. Not very much but I product. I didn't have equipment to test it and I'm not quiet sure of the effect of 3-methoxy,4-hydroxyphenethylamine. Nor would I like to be the first to find out.

Too bad vitride isn't avalible it would make things easier.


aldol - 10-3-2005 at 19:31

thank for the info on the murcury salts that would help but you still have to do a filtration somewhere thats the problem
i would like some info on the reduction of the oxime i think two stepping is a larger scale way of doing it direct reduction is way to small for me i didnt put all my efforts for small amounts regards aldol
thank heps for the tips shorly someone has done a large scale reduction from the oxime i will love you heeps

runlabrun - 11-3-2005 at 17:00

You originally said you ran the method using 30 p2np.... which is not large scale...
The method i posted can be scaled up but as far as i know not as far as a normal Al/Hg.... I think the only concerns you would have with scale on the urushibara would be stirring and temperature control, to far and it might get nasty... The footnotes on the page mention the yield can be increased a bit by using heavy overhead stirring, this would be essential if you were to scale it up at all...

What size batch(s) are you refering to when you say large scale??? With any reduction path there is a certain limit...


aldol - 11-3-2005 at 18:09

hi lab run lab
the 30 gram method i posted was the amount used to work method out
i have since done the tin reduction on a 2kg amount the results were the same
this reaction happens at a fairly lo temp
just keep adding acid until all the nitro is gone you will have a clear water layer when finished i have tried this with alcohol the results were the same
after basifiying you wont beleave how clean things are you will think were is the mess , there is none the bigger the amount the longer it takes
i think it is the same as the stanous chloride method to the oxime the only
difference is you are producing stannous chloride in sitsu slowly from the reation
which i think gives a lot less polermerization.
than stanous chloide
it is a brilliant way to the oxime
basifiying the oxime allowes you seperate the oxime from the salts and the hydroxides
i just need a reliable reduction of the oxime i have done the urashabara method on a small scale very messy
benz- NITRO - HUGE


enima - 12-3-2005 at 03:21

Al/Hg is good for reducing oximes. :)

Also Ammonium Formate and Zinc work ok.
I think you may get higher yields from Ammonium Formate and Magnesium.
For these proceedures make sure your oxime is recrystallized and pure as possible.

I'm gonna go ahead and say it, I personally don't condone the synthesis of amphetamines or their nastier n-methyl brother, but to each their own. This is chemistry after all :)

Btw. the ammonium formate is easily made via ammonium carbonate and formic acid. Titrate to a nice pH of 7 and remove the water.

Ammonium carbonate is sold as Bakers Ammonia.

[Edited on 12-3-2005 by enima]


aldol - 12-3-2005 at 12:34

thanks enima
i no tat most people on this site dont like
if i had as much piperanol as i have benz i would not be using benz
but when i get the oxime reduction working i will be looking out for piperanol
i would much rather do the reduction
on p2np than muk around with pills
if you muk with pills you will get court
i can go to p2p but the procedure is to long
enima thank for the refs on the oxime reduction havent seen that way before
regards aldol

enima - 12-3-2005 at 15:32

Synthetic Communications 34(4), 599-605(2004)
for the magnesium catalyzed reduction. I believe its also aval. on rhodiums website (one of the mirrors)

Typical Procedure

To a solution of the substrate (10 mmol) in methanol or in any other suitable solvent (20 mmol) was added ammonium formate (30 mmol) and magnesium powder (1g, 0.041 mol). The mixture was stirred under nitrogen atmosphere at room temperature. The reaction was exothermic and effervescent. After the completion of reaction (monitored by TLC), the reaction mixture was filtered through celite. The organic layer is evaporated and the residue was dissolved in chloroform or dichloromethane or ether and washed with saturated sodium chloride solution to remove excess ammonium formate. The organic layer was dried over anhydrous sodium sulphate and evaporation of the organic layer followed by purification either by preparative TLC or by column chromatography to yield the desired product.


aldol - 12-3-2005 at 17:38

thanks enima
the method looks good
isnt amonium formate the by product of the ammonium chloride and formilin condensation [ methylamine ]
i think i no that nasty smell it disstills of first
correct me if i am wrong :cool:
regards aldol

enima - 12-3-2005 at 19:00

I'm not sure exactly, hehe but methylamine is a foul smelling chemical.

You could use ammonium chloride to reduce the oxime. If you are going to be using the zinc method dont forget to activate the zinc via stirring it in dilute [hydrochloric] acid (5-7% generally) otherwise yields will be very low.

[Edited on 13-3-2005 by enima]


aldol - 13-3-2005 at 01:47

i no whae you mean about foul smell
been a long time but never forget the
smell , like stail pussy
getting back to the reduction the amalgam way sounds ok
i cannot use hcl because of the formation of p2p whitch rules out a clemenson reduction or any reduction involving acid
is this theary correct ?
i would like to no your thoughts
and can you use nicl instead of hgcl for the amalgam
regards aldol:cool:

enima - 13-3-2005 at 11:39

The zinc ic activated in the hcl solution, which is then filitered and washed with water to remove the acid. 2-3 washes with 100-200ml of water on 20g of zinc generally gets rid of most of the acid.

Unfortunately, no, you cannot replace the mercury salt with NiCl2.


aldol - 14-3-2005 at 20:20

thank enima i did,nt think you could

There must be someone out there that has done sodium in alcohol reductions of oximes HAVE LOT OF N/A METAL
i used to have 3 edition vogul
the method is in there but lost it
if it works for vogul it will work for me
and does the oxime have to be in base form for reduction
and can it be scaled
i would much rather use sodium metal than mercury salts
it looks like no one is comenting
i will have to try and tell
regards aldol


aldol - 15-3-2005 at 14:56

hi enima
the ammounium formate method looks good i thought that the formate had to be used with pd/c for direct reduction to the amine
my research said that it will reduce oximes to amines on a large scale
could you show me the mechanism
of this reaction
? between oxime magnesium and ammounium formate
and any tips to do this
any help would be appreciated

Edit: merged this with the existing thread.

[Edited on 3-16-2005 by Polverone]

some oxime reductions from rhodium's site

people eater - 25-3-2005 at 00:29

I imagine you could base your work on Sonson's Na reduction of mdp2p oxime or on another oxime reduction mechanism his references describe-

Step 2. Reduction of the oxime.

3.86g (0.02 mole) oxime was dissolved in 50 ml dry ethanol (fresh 99.5% is OK, otherwise look in Vogel for a procedure for making anhydrous EtOH with Mg and I2) in a two-necked 250ml roundbottomed flask equipped with a condenser, a cork and a stirring magnet. The reaction mixture was heated to reflux, the heat was turned off and 5g elemental sodium was added in such rate that a steady reflux was maintained (make 20-30 pieces and store under hexane). The first additions is conviently kept small. (NOTE: Hydrogen evolution). At the end the reaction was slower so the heating mantle was turned back on to speed things up. The waterwhite, clear postrxn mixture was then slowly treated with 16g H2SO4 in 200ml cold water. The EtOH was removed under vacuum, and the resulting water phase was washed twice with DCM. The aq. phase was made basic by addition of 25% NaOH. The freebase was extracted with 3x30ml DCM. The pooled organic extracts was evaporated under vacuum to constant weight leaving a pale colored residue (3.36g, 94%).

The freebase was dissolved in 20ml IPA, neutralized with 1.6ml HCl and percipitated by the addition of 40 ml Et2O. The crystals was filtered and washed with a small amount of Et2O. Yield: 3.4g of white MDA-HCl. Mp 187.5-188.5°C. (Litt: 187-188°C)

This reduction can also be done in n-BuOH according to [5], and with quite a few NaBH4 reduction systems (NiCl2[6], TiCl4[7], MoO3[8], Co-PC[9], amberlyst-15+LiCl[10], and even with plain NaBH4 in EtOH according to [11]). Adding NaOH to a suspension of Ni-Al is also said to reduce oximes[12] as is SnCl2-Sn-HCl[13].

Different synthesis of oximes starting with nitroalkenes should be looked into, as this could be a good alternative to the existing methods for reducing nitroalkenes. SnCl2 reduces nitroalkenes to oximes under both acidic and basic conditions[14, 15, 16). Zn(BH4)2 in 1,2-DiMeO-ethane does reduce 3,4-MD-phenyl-2-nitropropene to the oxime in good yields [17]. Another promising route is the use of Pb in DMF [18]. This seems to reduce most nitroalkenes to the corresponding oximes.

1. J. Pharm. Sci. 69; 2; 1980; 192-195
2. CA 1955;10595
3. Chem. Ber. 114;12;1981;3813-3830
4. J. Chem. Soc. Perkin. Trans. 2;2;1997;249-256
5. JACS 56, 487 (1943)
6. Chem. Pharm. Bull. 36;1988;1529-1533
7. Synthesis 9;1980;695-697
8. Chem. Ber. 117;2;1984;856-858
9. Angew. Chem. 93;5;1981;477-479
10. Syn. Lett. 4;1999;409-410
11. J. Chem. Soc. Perkin. Trans. 2; 1980; pp83-86 (very sparse information)
12. Aust. J. Chem 34; 1;1981;45-56
13. JACS 67;1945;496
14. Tetr. Lett. 26;49;1985;6013-6014
15. Synth. Commun. 18;7;1988;693-698
16. Heterocycles 24;9;1986; 2581-2586
17. Tetrahedron 48;25;1992; 5317-5322
18. Tetrahedron 48;21;1992; 3313-26 among others

Or you could adapt Antibody2's Al/Hg/AcOH reduction of mdp2p oxime-


In a 4l beaker with mag stirring, 0.75 moles of activated Al (19.5g) [1] is added to 1l 95% EtOH and 100mls dH2O, followed by 0.33 moles oxime of MDP-2-P (65g) [2],and 3 moles HOAc (180g). The Rxn is heated to 60C and heat removed. There follow three additions of 0.75 moles of activated Al at 30 minutes, 1 hour, and two hours. Temperature was maintained at 60C by placing beaker in a cold water bath as necessary. There is a vigourous evolution of hydrogen as the rxn progresses, care must be taken the rxn vessel does not overflow. An additional 150mls 95% EtOH and 15mls dH2O is added at 2hours. At 3 hours the rxn is a viscous gel which has stopped the stir bar. An additional 300mls 95% EtOH and 30mls dH2O is added . The rxn was allowed to stir until it has returned to room temperature, during which time 1 l of 15M NaOH was prepared and cooled. The rxn vessel was placed in a cold water bath and the basic solution was added slowly over 20 minutes, with care being taken the tempertaure did not rise above 60C. 500g of NaCl was added, much of which precipitated after stirring. 500mls toluene is added with stirring. The toluene/EtOH/amine layer is separated and decanted into 750mls of dH2O, causing the EtOH to migrate to the aqueous layer. The toluene layer is separated and the aqueous/alcoholic layer is extracted 2 times with 250mls toluene. The pooled toluene extracts are washed once with 400mls dH20 and once with 400mls brine, then dried through MgSO4 and gassed w/ dry HCl gas, furnishing 54g MDA HCl (0.267 moles, 81%) .

1. Activated by refluxing in 19.5g Al in 800mls of 50/50 dH2O/MeOH, with 1g Hg2Cl2 for 15 minutes, the mercuric solution was decanted, and Al was washed once with 400mls 95% EtOH, which was also decanted. Same mercuric solution was used for all four activations.
2. Prepared according to Sonson's instructions

Note from zee pourple people eater-

You can simply amalgamate the aluminum in situ for convenience and 1g of Hg salt would be huge overkill I think. HgI2 is easily prepared by briefly stirring .5g Hg, .66g I2, 1-2ml MeOH. it can be used immediately or allowed to evaporate to a uniform red powder. Conc h2so4 is the best for getting the post amalgam grap out of yer flask. If you use toluene/xylene for extraction, you have to add enough water (with base) to make the acqueous layer denser than the toluene/xylene, or it won't separate properly. With this in mind it's idiot-proof, persuming your oxime is as good as ours. Not that we ever had p2np, but p2np should easily hold up to the conditions that its ring-substituted relatives can.

Can someone tell me more about the ease and scaleability of nitropropene reduction systems which use Ni- urishibara, base catalyzed, and raney nickel? Also info and the refs for the NaBH4/metal oxime reductions are of interest.


aldol - 25-3-2005 at 02:38

hi people eater
just some thought for you i have played with all sorts of p2np reductions all the desolving metal ways to the amine are not going to be very big
just a bit more work to 2 step either to the nitroalkane or via the oxime or make p2p far eisier to go to the oxime and then reduce the oxime to the amine.
LOOK at my ,oxime procedure very good no bullshit it works
i have sonsons reduction method of the oxime i am going to use it.
it is the same method i had in my 3rd edition vogul untill it got lost
thanks heeps people eater for the trouble you went to, I hope my method helps you .
dont overlook it
regards aldol

Sandmeyer - 15-6-2005 at 09:29

There is a way to reduce the C=C bond conjugated to an electron-withdrawing group, (like in nitrostyrenes) using p-dihydroxypyridines which be made from readily available aliphatic precursors.

Diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

A mixture of ethyl acetoacetate (20 mmol), hexamethylenetetramine (8 mmol) and ammonium acetate (10mmol) is irradiated for 100s (45W, Synthewave S402). After cooling, the solid is filtered, washed with ethanol and dried under vacuum; m.p. 188-190°C

Typical procedure for the reduction of olefins by DHP

Silica gel (4g), nitrostyrene (0.6g, 4 mmol) and DHP 1a (1.5g, 6 mmol) are diluted in methylene chloride (20 mL). The solvent is quickly evaporated in vacuo. The resulting solid is irradiated for 4 min (150W, Synthewave S402) under a nitrogen atmosphere, cooled and filtered. The filtrate is stirred for 20 min with 6N HCl (20 mL). The organic layer is dried on MgSO4 and concentrated in vacuum to afford 2-phenylnitroethane (yield 78%)

iron filings and hydrochloric acid

Rosco Bodine - 15-6-2005 at 14:32

If you have some means of good stirring ,
such as a rapid reversing agitator which works something like a washing machine agitator , but goes about four full revolutions each direction , you can run
a very efficient conversion of phenylnitropropylene to phenylacetone at about 95% yield of .999 fine product in
one step .

The PNP is added to dilute aqueous ferric chloride and iron filings and the mixture is heated and stirred until the PNP melts and begins to emulsify , then concentrated HCl is gradually added ,
at such a rate as the heat of reaction
allows . A water trap with a sample takeoff or return to reaction 3 way stopcock is interposed between the reaction flask and a tall reflux condenser
placed above the water trap . Until the addition of the HCl is complete and the reduction finishes , all of the reflux is returned to the reaction .

As the reduction of the PNP proceeds , first the oxime is formed as an intermediate , but in the acidic reaction
mixture the oxime is further converted to the ketone , which will steam distill from
the mixture and accumulate in the water
trap with phase separation , from the water . In order to make the phase separation occur cleanly instead of having
a milky emulsion of phenylacetone and water accumulating in the trap , some addition of benzene to the reaction flask
will give a twofold benefit , in that the separation of the desired product with benzene occurs cleanly , and due to the lowered density becomes the upper layer
in the water trap , so that the valve can be adjusted to return the separated lower
layer of water at about the same rate as it
accumulates , so that the water layer in the trap remains low as the phenylacetone layer steadily increases and is drawn off periodically . The pure
phenylacetone is easily separated from its
solution in benzene simply by heating gently to drive off the far more volatile benzene . IIRC , a small amount of hydroquinone should be added to the
phenylacetone as an anti-oxidant preservative and polymerization inhibitor ,
prior to any isolation , vacuum distillation ,
or storage of the material , as it is subject to the same instabilities as is typical of other similar ketonic-aldehydic substances like for example benzaldeyde .

[Edited on 15-6-2005 by Rosco Bodine]

alcoholic hydrazine and 5% palladium on charcoal

Rosco Bodine - 15-5-2012 at 02:32

Hydrazine reduction of phenylnitropropene...
imagine that...what a curious coincidence :cool:
This appears interesting and I don't recall seeing this having been mentioned. US2768209 describes P2NP reduction using hydrazine in alcohol ....See the patent title elaborated briefly in the next to last paragraph of Example 8 .....

Of course what I probably meant to say is regardless of the patent title there is likely nothing of interest here except this shows a good possible analogous method for reduction of m-dintrobenzene to m-nitroaniline See Example 5. Pay no attention to the patent title, move along, these are not the droids you are looking for :D

Attachment: US2768209 Hydrazine reduction of phenylnitropropene.pdf (180kB)
This file has been downloaded 1686 times

Tsjerk - 15-5-2012 at 03:34

In the last paragraph of example 8 the author is talking about reduction to yield 2-amino 1-phenyl propene-1 and claiming that this is amphetamine. But the amphetamine is the propane.

Would this reduction yield the fully reduced product or the propene?

ScienceSquirrel - 15-5-2012 at 04:19

Quote: Originally posted by Tsjerk  
In the last paragraph of example 8 the author is talking about reduction to yield 2-amino 1-phenyl propene-1 and claiming that this is amphetamine. But the amphetamine is the propane.

Would this reduction yield the fully reduced product or the propene?

It is a typo, the product is the propane.

Rosco Bodine - 15-5-2012 at 04:32

It appears likely that the reduction is likely complete and the propylene is converted to propane ......however there is a journal article by the inventor which is likely to have additional detail. File attached below, thanks to solo.
Hmmm....not one mention of amphetamine appears in the journal article, and yet six months later a patent application is made taking five years more to issue, a patent making one and only one claimed compound added to the list of those published in the journal article......very interesting huh. :D

Catalytic Reduction with Hydrazine
Lester P. Kuhn
J. Am. Chem. Soc.
1951, 73 (4), pp 1510–1512
DOI: 10.1021/ja01148a029

Attachment: Catalytic Reduction with Hydrazine.pdf (387kB)
This file has been downloaded 1429 times

There are similar methods using hydrazine and either powdered zinc or powdered magnesium which are mentioned. It would seem that the hydrazinium monoformate reagent could be formed in alcohol by alternate schemes using hydrazine sulfate as a starting material with added steps. So it appears there are 3 schemes by which hydrazine may be useful for the reduction of phenylnitropropylene to the "methylphenylethylamine" or "phenylisopropylamine" or amphetamine.

Maybe we should ask "Dr. Know, M.D." since he is a medical doctor and knows about this complicated Jedi mind trick kind of stuff ;)

[Edited on 15-5-2012 by Rosco Bodine]

[<a href="u2u.php?action=send&username=bfesser">bfesser</a>: this is not a politics thread; replaced image with link]

[Edited on 7/7/13 by bfesser]

Hydrazine Sulfate reduction of Nitrourea to Semicarbazide

Rosco Bodine - 28-3-2013 at 20:24

Here is another obscure reaction showing the reduction of a nitro compound by Hydrazine.

GB790066 Semicarbazones via Hydrazine and Nitrourea

I did a search to see if GB790066 had ever been brought up by anyone before as a matter of interest

But the patent GB790066 says that the (apparent) "reduction" of produces N2O as a byproduct and nitrous oxide would not be expected from an ordinary reduction where H2O would seem to be the anticipated byproduct. Strange and interesting. A similar unexpected modified "reduction" may also occur when hydrazine is used for "reduction" of other nitro compounds.

The reduction of nitrourea by hydrazine to semicarbazide is not a conventional reduction, but involves formation of an unstable intermediate hydrazine salt of nitrourea, which decomposes with evolution of nitrous oxide ....similarly perhaps as does ammonium nitrate decompose under certain conditions to evolve nitrous oxide. So after 10 years the subject of GB790066 is being revisited. This thread seemed as good a place as any from which to reflect. :)

Attachment: GB790066 Semicarbazide from Nitrourea and Hydrazine Sulfate.pdf (361kB)
This file has been downloaded 581 times

[Edited on 29-3-2013 by Rosco Bodine]

chemrox - 28-3-2013 at 21:26

Quote: Originally posted by enima  

I'm personally don't like metal + hcl reductions they are very unreliable and yields are piss poor.

The workup from MD-nitrostyrene after using HCl and Fe was messy and involved a lot of liquid. I think it's time to brave the LAH "barrels." Or the HgCl2/Al foil.

chemrox - 28-3-2013 at 21:28

Quote: Originally posted by Rosco Bodine  

Maybe we should ask "Dr. Know, M.D." since he is a medical doctor and knows about this complicated Jedi mind trick kind of stuff ;)

[Edited on 15-5-2012 by Rosco Bodine]

Let's just ask him for money. That he does know.

Rosco Bodine - 28-3-2013 at 23:14

Gresham's Law Enforcement .....
it's a tough job but somebody has got to do it.

A penny saved a long time ago is worth more than the penny made now.

Who ya gonna call when Gresham's Law has done its deed on the zinc?


Wooden nickels are the coin of the future. Hey that's real "progress" huh. :D

S.C. Wack - 29-3-2013 at 18:12

Preferred coinage: Canadian Pd Maple Leafs and the various sizes of US Mint Pt.

Note US3458576 for uses of Pd without hydrazine.

Hydrazine hydrate is interesting with Ni reductions as well.

Mildronate - 30-3-2013 at 00:37

Its very easy to reduce it with aluminium amalgam or with urushibara nickel. If you whant ketone then you can reduce it with fe/hcl.

[Edited on 30-3-2013 by Mildronate]

Rosco Bodine - 30-3-2013 at 08:59

Quote: Originally posted by S.C. Wack  
Preferred coinage: Canadian Pd Maple Leafs and the various sizes of US Mint Pt.

Note US3458576 for uses of Pd without hydrazine.

Hydrazine hydrate is interesting with Ni reductions as well.

Yeah it seems we have a "reductive hydrazination" or reductive amination aspect about some of these complex reductions through an intermediate....distinctly different from a straightforward reduction by hydrogen for comparison.

LOL :D Another like me, a believer in the "divine right" to keep and bear gold, silver, platinum, and any arms which may be needed to assure its continued possession in spite of "tax collectors" evil ambitions to divert it to their own enrichment under false pretense such theft serves what the thief would estimate is the genuinely "greater good" by that thief simply taking and spending what is rightfully anothers. Beware of the thief in the night and even moreso beware of the thief who so boldly, brazenly comes by day. Revenuers are just no damn good, and they have been around since liars and thieves were invented :o

palico - 22-2-2015 at 16:44

I had a dream also. I reduced phenyl-2-nitropropene simply with metallic sodium in ethanol.
Can this dream become reality ?
Anyone has ever tried this workup ?
What's wrong with this simple method ?