I am working on reducing an aromatic nitro group to amine and have tried SnCl2 and Fe systems without much luck. There are literature examples of this compound being reduced by H2 gas with Pd/C and a related compound being reduced with formic acid and Pd/C, all at room temperature or 0 C, with the formic acid reactions conducted open air.

I have wet Pd/C catalyst and have tried a variety of set-ups with ammonium formate and formic acid (no H2 gas for me) and have never gotten product, though I have gotten what by TLC appear to be the nitroso and hydroxyl-amine forms potentially. I have noticed that upon addition of catalyst or hydrogen donor to my stirring mixture I see no bubbles produced.

I understand that the catalyst should be more than happy to convert formic acid into CO2 and H2 regardless of the nitro substrate. Is there a way to check if my catalyst is inactive, or am I missing some necessary activation step since I do not seem to be seeing CO2 production?

Thanks

Update:

Thanks for the ideas everyone. I'll try transfer hydrogenation one more time with a new (hopefully more active) catalyst. If that fails I'll give iron and ammonium chloride a shot.

Final update: I think it was bad catalyst. I added double what I normally would and set-up oxygen free and saw moderate bubbling through a bubbler and saw substrate converted all the way to arylamine product.

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