Sciencemadness Discussion Board

I need to reduce a nitro to amine. Idea ?

Methyl.Magic - 17-7-2008 at 08:18

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]

Klute - 17-7-2008 at 11:24

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]

Ritter - 17-7-2008 at 11:34

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.

Methyl.Magic - 20-7-2008 at 08:42

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 !