How to carry out reduction of N-(4-nitrobenzyl)-1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine to 4-((bis(pyridin-2-ylmethyl)amino)methyl)aniline?

25 January 2023 1 5K Report

I have tried the reduction of 4-nitrobenzyl moiety in the ligand by using SnCl2.2H2O many times but unfortunately, I got a degraded product. then I tried H2 in presence of Pd/C. this time also I got a degraded product. I got dipicolylamine every times. Kindly suggest some explanation for this. what should I try to carry out this reaction?

Kyle A. Grice

Hello,

I second trying NaBH4 in MeOH/EtOH.

Pd/C is known to remove benzyl groups, so that makes sense that it does that.

Iron metal in acid is another approach. You could try Zn/acid or Fe/acid. Article Reduction of aromatic nitro compounds to amines using zinc a...

-KYle

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