Methyl.Magic
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I need to reduce a nitro to amine. Idea ?
Hello !
I have a nitro group and I need to reduce it into amine. The substrate doesn't have any sensible group. I know several method but I only have have 1g
of the substrate... so I need to choose the best reduction pathway. Your propositions are welcome ! Thank you !
Methyl.Magic
The substrate is :
3-(2-nitro-1-phenyl-ethyl)indole
I have at hand :
- Pd/BaSO4
- HCOOH
- HCOONH4
- Zn, Fe, Sn, Ni, Mg powder
- HgCl2
- LiAlH4, NaBH4, TiH2
- Copper chromit catalyst
- RuCl3
[Edite le 17-7-2008 par Methyl.Magic]
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Klute
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Definitively go for a CTH, I think even a desactivated catalyst such as Pd/BaSO4 could reduce it effectively, might need to add more cat. and longer
reaction times.
LiAlH4 would be a bit of a waste, but should work no problem.
PS: in case you ahevn't rea dit already, there is a thread on CTH reduction of nitro compounds detailing sevral procedures and their optimization.
[Edited on 17-7-2008 by Klute]
\"You can battle with a demon, you can embrace a demon; what the hell can you do with a fucking spiritual computer?\"
-Alice Parr
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Ritter
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| Quote: | Originally posted by Methyl.Magic
Hello !
I have a nitro group and I need to reduce it into amine. The substrate doesn't have any sensible group. I know several method but I only have have 1g
of the substrate... so I need to choose the best reduction pathway. Your propositions are welcome ! Thank you !
Methyl.Magic
The substrate is :
3-(2-nitro-1-phenyl-ethyl)indole
I have at hand :
- Pd/BaSO4
- HCOOH
- HCOONH4
- Zn, Fe, Sn, Ni, Mg powder
- HgCl2
- LiAlH4, NaBH4, TiH2
- Copper chromite catalyst
- RuCl3
[Edite le 17-7-2008 par Methyl.Magic] |
Your problem is to find the correct reagent & conditions that will reduce the benzylic nitro group without reducing the indole to the indoline.
You could run a series of microscale reduction experiments but if you lack authentic samples of the aminoindole, nitroindoline & aminoindoline
then you will not be able to check your progress via TLC.
Havbe you checked the literature for these compounds & secured the literature references where they were prepared & characterized? The best
time to ask for recommendations is when you have already defined your various options.
Ritter
=============================
\"The production of too many useful things results in too many useless people.\"
Karl Marx
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Methyl.Magic
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ok thank you for the help !
Ive found that topic on the CTH nitroalkane reduction : http://sciencemadness.org/talk/viewthread.php?tid=8929&p...
Steeve got 97% with the CTH reduction of nitroalkane. It seems very effective and easy !
Thank you !
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