Reactions of Tertiary Butyl Hypochlorite. I. The Chlorination of Aromatic Nitroamines

Abstract

Tertiary butyl hypochlorite reacts with 2-nitroaniline, 4-nitroaniline, N-methyl-4-nitroaniline, and NN-dimethyl-4-nitroaniline to form excellent yields of nuclear-chlorinated derivatives. Direct oxidation, to form azo compounds, is also observed with 4-nitroaniline and the yield of azo compound increases at higher temperatures. Demethylation also occurs when N-methyl-4-nitroaniline and NN-dimethyl-4-nitro-aniline are used.