Reduction of polyfunctional aromatic nitro compounds using lithium aluminium hydride

Aromatic nitro compounds containing yet another functional group are reduced using lithium aluminium hydride in ether. The reduction of nitrobenzanilides results in preferential reduction of amide functionality while the isomeric N-(nitrophenyl) benzamides results in preferential cleavage of the amide bond. Be sides, the reduction of 2,2'-dinitrodiphenyl amine 5a, reduction of (bis-2-nitroanilino) methane 5b, 2, 2'-dinitrodiphenylether 5c, 2-nitrophenyl-2'-nitrophenoxymethane 5d, 1, 3-dinitrobenzene 6a, 2-nitrobenzaldoxime 6b, 2-N (2'-nitrophenylmethyl) amino benzoic acid 6c, 2-nitrophenoxymethyl phenyl ketone 6d are carried out. Nitro group is found reluctant towards reduction in some cases whereas in some others it is reduced into different extents. This points to the limitation of the suggested azo test for aromatic nitro compounds.