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Author: Subject: Indole Synthesis
Waffles SS
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[*] posted on 19-12-2009 at 01:57
Indole Synthesis


Fischer indole synthesis:






It seems this is not very difficult.
Anybody has experience/suggestion/better or easier method?


.Fischer, E.; Jourdan, F. Ber. 1883, 16, 2241.
.Fischer, E.; Hess, O. Ber. 1884, 17, 559.
.Van Orden, R. B.; Lindwell, H. G. Chem. Rev. 1942, 30, 69-96.
.Robinson, B. Chem. Rev. 1963, 63, 373-401.
. Robinson, B. Chem. Rev. 1969, 69, 227-250
Source:wikipedia
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sonogashira
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[*] posted on 19-12-2009 at 02:37


I haven't, but you can look here http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0479 in 'discussion' section for alternatives. There is also book called - Indoles best synthetic methods - which you may find interesting. Best luck!

[Edited on 19-12-2009 by sonogashira]
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Waffles SS
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[*] posted on 19-12-2009 at 03:29



Quote:

passing a mixture of acetylene and aniline through an iron tube at 700.

Majima, Unno, and Ono, Ber., 55, 3854 (1922).

I heve ketene Equipment therefore i think is usefull for this method too.
Anybody has idea or instruction for this method?

[Edited on 19-12-2009 by Waffen SS]
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Nicodem
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[*] posted on 19-12-2009 at 05:55


Indole itself can not be prepared from phenylhydrazine and acetaldehyde using the most common conditions for the Fischer indole synthesis. The reaction is possible, but requires quite some modified conditions. I already posted about this (references included) in some old thread about the same subject, so UTFSE to find it. However, Fischer indole synthesis can be used to prepare indole indirectly by decarboxylating 2-indolecarboxylic acid prepared from phenylhydrazine and pyruvic acid.



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Waffles SS
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[*] posted on 19-12-2009 at 06:14


Quote: Originally posted by Nicodem  
However, Fischer indole synthesis can be used to prepare indole indirectly by decarboxylating 2-indolecarboxylic acid prepared from phenylhydrazine and pyruvic acid.

Thanks @Nicodem but I need reaction instruction?amount?temp?...?
You have it?


[Edited on 19-12-2009 by Waffen SS]
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sonogashira
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[*] posted on 19-12-2009 at 07:14


Here is an indole chemistry review. See what is best method to you and then ask for the references for the experimental :)


Attachment: cr60095a004.pdf (301kB)
This file has been downloaded 6667 times

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entropy51
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[*] posted on 19-12-2009 at 07:30


Quote: Originally posted by Nicodem  
There is no method to prepare indole itself by using the Fischer cyclisation.
Utmost it is possible to prepare indole-2-caboxylic acid with the Fischer cyclisation of pyruvic acid phenylhydrazone. Indole-2-caboxylic acid can then be decarboxylated to indole.
If you follow that quote back to the thread it came from (click on the green ->;), Nicodem gives some advice about how to find the type of information you seek.
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Nicodem
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[*] posted on 19-12-2009 at 07:37


Quote: Originally posted by Waffen SS  
Thanks @Nicodem but I need reaction instruction?amount?temp?...?
You have it?

Sonogashira already gave you the link to the Org. Synth. entry where you could have looked up for these references:

"Indole-2-carboxylic acid has also been prepared by the Fischer indole synthesis from pyruvic acid phenylhydrazone catalyzed by zinc chloride" : E. Fischer, Ann., 236, 141 (1886); Ber., 19, 1563 (1886).

"...followed by reduction to indole-2-carboxylic acid and decarboxylation of the latter" : Reissert, Ber., 30, 1045 (1897).

Both journals are available online, so you do not even have to visit a library. There surely are other references for this process, but I leave the literature search to others.




…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)

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Waffles SS
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[*] posted on 19-12-2009 at 08:48


phenylhydrazone?
Unfortunately i have access just to phenylhydrazine but i dont have information on phenylhydrazone synthesis.
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Nicodem
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[*] posted on 19-12-2009 at 11:48


Huh?
Am I mistaken or you never bothered to read about the mechanism of the Fischer indole synthesis even though you posted the scheme of it in the first post above?
I suggest you to check that scheme again, because it nicely says "phenylhydrazone" under the first reaction intermediate.
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entropy51
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[*] posted on 19-12-2009 at 13:26


Waffen, I told you that making ketene without a fume hood wasn't good for you!:P
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Waffles SS
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[*] posted on 19-12-2009 at 13:37


Ohhhh.
Excuse me i mistaked.
Iam interesting on Reissert indole synthesis because i think is cheaper and easier.
But i dont know instruction and dont have access to online journal(all of online journals that i know arent free).



Reissert, A. Ber. 1897, 30, 1030.
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Nicodem
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[*] posted on 19-12-2009 at 15:19


Quote: Originally posted by Waffen SS  
Ohhhh.
But i dont know instruction and dont have access to online journal(all of online journals that i know arent free).

Reissert, A. Ber. 1897, 30, 1030.

But Berichte is free: http://gallica.bnf.fr/ark:/12148/bpt6k907462.pleinepage.f103...

Using the search engines to obtain information is always a good idea.
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Peroxid
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[*] posted on 19-12-2009 at 15:24


This is a modified method (the first step is same), but maybe it will be useful!

http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0567

[Edited on 19-12-2009 by Peroxid]
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[*] posted on 19-12-2009 at 17:23


Out of interest, if one was to heat a homogenous mixture of NaOMe (commercial) and N-formyl-o-toluidine to a high temperature as per http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0479 , would the indole be expected to distill off in a reasonable (but lower than that using K-t-BuO) yield? Any need for an initial solvent, or would dry distillation theoretically suffice?

"The cyclization of N-formyl-o-toluidine with sodium in methanol has been described and is recommended as a safer and less expensive method than that involving the use of potassium metal." Galat and Friedman, J. Am. Chem. Soc., 70, 1280 (1948).
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[*] posted on 19-12-2009 at 23:56


@Nicodem,thanks i know Reissert was from deutschland but i dont know germany.

[Edited on 20-12-2009 by Waffen SS]
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[*] posted on 20-12-2009 at 02:23


Quote: Originally posted by Waffen SS  
@Nicodem,thanks i know Reissert was from deutschland but i dont know germany.

Then why the hell do you use such an irritating german username? Just to annoy us or what? And why did you ask for the information if you did not want it in the first place? And what does it matter if it is in german? Have you never heard of dictionaries and translation machines?

For the internet challenged: http://translate.google.com/

This is the last time I help you. Now I give up. :(
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JohnWW
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[*] posted on 21-12-2009 at 16:42


After the War/Whore, members (or at least officers) of the Waffen SS (who were a large elite para-military secret police force, responsible for rounding up and deporting Jews and other dissidents in Nazi-occupied areas to death camps, mostly on the eastern front) were prosecuted in war crimes courts for belonging to a criminal organization. (SS = Schützstaffel). See: http://en.wikipedia.org/wiki/Waffen-SS , http://www.waffen-ss.com , http://www.jewishvirtuallibrary.org/jsource/holocaust/waffen... , http://en.wikipedia.org/wiki/Police_forces_of_Nazi_Germany , http://en.wikipedia.org/wiki/Category:Nazi_SS , http://en.wikipedia.org/wiki/Schutzstaffel , http://en.wikipedia.org/wiki/Gestapo .

I hope you were not among them. You would have to be at least 80 now, to have been; Pope Rat was conscripted into the SS in early 1945 at age 17, one of its youngest members.

BTW When you made your indole, how did you deal with, or suppress, its intense fecal smell? Did you wear a gas mask? Did the neighbors complain? Ironically, in very small amounts, the stuff is used in perfumes.

[Edited on 22-12-09 by JohnWW]
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entropy51
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[*] posted on 21-12-2009 at 17:06


Well, John, for once I have to agree with you (I always agree with Nicodem, I'm no dummy), this does seem to be a fairly obnoxious user name. Waffen SS, why don't you re-register with a user name that evokes less memory of crimes against humanity. If not for moral reasons, then because Nicodem is not a source of information to disregard lightly.

John, he hasn't made any indole. He seems to be unlikely to make indole or anything else. Probably not a bad thing.

[Edited on 22-12-2009 by entropy51]

[Edited on 22-12-2009 by entropy51]
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Waffles SS
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[*] posted on 21-12-2009 at 23:47


My believe is my believe and this is chemistry forum nothingelse,sure i have acceptable reason for my choice and my believe.
back to chemistry
I wanna use indole(iaa,iba) as hormone in some trees(for fast growing,..)

[Edited on 22-12-2009 by Waffen SS]
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[*] posted on 22-12-2009 at 00:38


Have you read the literature on using IAA on woody plants and trees? From what I recall, it really is only effective for the first few months from sprouting, later on it just encourages root growth.

If you are planning the classic synthysis of IAA from indole and glycolic acid, you must have a stirred autoclave for running the reaction at 250 C / 40 atmospheres pressure.



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[*] posted on 22-12-2009 at 07:24


Indole as a growth hormone for plants? Actually, it is indole-3-acetic acid, or 2-(1H-indol-3-yl)acetic acid, that is used for this purpose, see http://en.wikipedia.org/wiki/Indole-3-acetic_acid and http://www.super-grow.biz/IAA.jsp among others. It is probably the most important plant auxin, occurring naturally in the apical cells of growing plants. It can be synthesized by the reaction of indole with glycolic acid in the presence of base at 250°C.


[Edited on 22-12-09 by JohnWW]

File_Synthesis_of_indole-3-acetic_acid.png - 22kB
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[*] posted on 22-12-2009 at 08:02


Yes, the collection of spineless bullies did say "indole(iaa,iba)" where IAA is a common abbreviation of indole acetic acid, and IBA for indole butyric acid.

The Fischer synthesis can be used to directly produce IIA and IBA or simple derivatives of them, without going through indole in an intermediate step.



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Waffles SS
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[*] posted on 22-12-2009 at 08:42


I have problem with Fischer indole synthesis For making IAA.
@Nicodem said this reaction need special condition and he suggest Phenylhydrazone+Pyruvic acid but i need more detail about it.
Anyone can send refrence or instruction about that?
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entropy51
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[*] posted on 22-12-2009 at 08:44


Quote: Originally posted by Waffen SS  
My believe is my believe and this is chemistry forum nothingelse,sure i have acceptable reason for my choice and my believe.
In addition to a chemistry forum, it is a community. Some members of that community may have very personal reasons, such as the murder of relatives by the Waffen SS, to find your "believes" and reasons not acceptable. But suit yourself.
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