Reductions with Sulfurated Borohydrides. VI. The Reduction of Nitro, Nitrile, Amide, and Nitroso Groups

Abstract

Aromatic nitro compounds can be reduced with sulfurated sodium borohydride to the corresponding amine in high yields (≈80%) without affecting ester, nitrile, ether, halide or olefinic groups also present. With ortho-substituted nitro compounds the yields are around 60%.Primary aliphatic nitro compounds are reduced to the corresponding nitrile in high yields. Secondary aliphatic nitro compounds are reduced to mixtures of ketones and the corresponding oxime. Tertiary aliphatic nitro compounds are not reduced.Aromatic nitriles can be reduced to the corresponding amines with an excess of the reducing agent or converted to the corresponding thioamides with an excess of the nitrile.Amides and nitroso can be reduced to the corresponding amines in moderate yields.