Nitro to Amine by Iron powder: Why iron? Why not zinc? -Bechamp reduction

[@waynecooper6124]

This is an underrated and overlooked reaction with outstanding synthetic utility!! Great selection and presentation!

[@Dr.Mosharraf]

Thank you very much

[@jimparsons6803]

Liked the presentation. Clever use of a plastic straw as a spatula. Liked also the discussion and presentation of the mechanism.

[@Dr.Mosharraf]

Hi Jim, thank you for your comment. I am getting inspiration from all of you who are interacting in this channel. That is actually plastic spatula 😎🤓.

[@slavakuznetsov4966]

One of the easiest reactions to run. Occasionally I used EtAc or THF and acetic acid instead of 6N HCl and MeOH, large excess of Fe, and reflux ON. Excellent selectivity and complete conversion without by-products. Very nice as NH2 de-protection strategy

[@minusstage3]

Thank you friend. Enjoyed this!

[@Dr.Mosharraf]

Thank you

[@pajaroamarillo3713]

your channel is of very high quality! thank you for sharing your knowledge. i have seen this reaction before, ‘Bechamp’ but does it work on aliphatic compounds? i have always seen aromatics as an example for this reduction, is it possible to reduce aliphatic nitro compounds? Best regards! thank you for your knowledge

[@Dr.Mosharraf]

Tertiary carbon Nitro to amine by HSiCl3-A problem solved for sensitive multi functional groups. kzbin.info/www/bejne/jHnJkqGLbq-roqs Please watch this video. It is for aliphatic Nitro to amine. This video must’ve the literature reference too.

[@pajaroamarillo3713]

@@Dr.Mosharraf very thanks

[@priyavimal1234]

May I know your complete name please. So that I can go through your research paper as well.

[@Dr.Mosharraf]

scholar.google.com/citations?user=VgfR2FAAAAAJ&hl=en

[@priyavimal1234]

Thank you.

[@Dr.Mosharraf]

You are welcome

[@muaathe78]

can we use dichloro Ethane as a solvent instead of methanol to reduce nitro-polymer

[@Dr.Mosharraf]

DCM is worst solvent for hydrogenation but if your compound is not soluble in MeOH and if you need to use DCM then try using 50:50 DCM and THF. It may give you better result than only DCM.

[@muaathe78]

@@Dr.Mosharraf My polymer is soluble in DMF, THF and EtOAc

[@Dr.Mosharraf]

You can try 100% THF then.

[@عمارمازن-ه8ظ]

Pleas can you send me the Reference

[@Dr.Mosharraf]

pubs.acs.org/doi/10.1021/ja4080024. JACS 2013,135, 17408-17416

[@عمارمازن-ه8ظ]

@@Dr.Mosharraf Thank you very much

[@Dr.Mosharraf]

You are welcome 🤗

[@LolLol-jl3rl]

Won't HCl hydrolyze the ester ?

[@Dr.Mosharraf]

No for this reaction ester was intact. Logically it should be.

[@RehanAnsari-bg9ut]

Please sir help me I try to convert 5-nitrosalicylic acid to 5-aminosalicylic acid Please sir suggest me i am facing a problem to this conversation by reduction reaction Its my M pharm project second step Please sir help And guide me …

[@Dr.Mosharraf]

First make the carboxylic acid group to its methyl ester. Take acid in flask and dissolve it in anhydrous Methanol. Degas it and then add catalytic amount of H2SO4. Reflux it at 50 deg Celsius for at least 7-8 hours. Cool down the reaction flask. Then add 5% NaHCO3 solution (to remove unreacted carboxylic acid) and extracted with DCM. Then try with Zn in AcOH acid, or Fe in HCl, or FeCl2 method, or Sn+HCl or Cl3SiH method those are in my channel. After reduction, keep the pH near 7 and quickly extract with EtOAc. And then purify. The ester amine compound then can be converted to acid amine by dissolving the compound in Methanol and 10 M NaOH and reflux the solution at 50 deg Celsius for at least 12 hours. Then concentrate the solution to 1/10 th of its volume. Then add slowly 50 percent aqueous HCl solution slowly drop wise and check the pH with pH paper up to 7. It will be tricky because it will act as amino acid type behavior and if you can not adjust pH then it will produce zwitter ion. If you have preparative HPLC or semi Prep HPLC, you can easily purify with reverse phase column. Otherwise you can extract the compound with 5%Acetonitrile in EtOAc. Do multiple time extraction and then dry the solvent. Hopefully you will get the compound that should be pure. It will be difficult to say it is pure by NMR since it can stay as zwiter ion, some portion acidic, some portion basic. So you might see mixed peak in NMR. So, understand it is pure or not either make it basic pH above 8 or acidic like pH below 5, then do HPLC analysis to see how many peak you get. I hope this help you.