Reduction of nitroarenes to anilines in basic alcoholic media

Abstract

Substituted nitrobenzenes are reduced by alkoxide ions in alcohols to the corresponding azoxy and aniline derivatives. The reaction leading to anilines has been investigated in detail. Two different processes have been identified, both initiated by the condensation between the nitrosoarene intermediate (the first product of the reduction reaction) and the product of oxidation of the solvent. The imino derivative thus formed (ArNCH–COR) may either undergo hydrolysis (to aniline) or form, through a series of redox processes, compounds containing the ArNH–CO moiety. These are also hydrolysed to anilines in a slower reaction.