Oxidations with iodosobenzene diacetate. X. The Oxidation of 3 (or 6)-Substituted-2-nitroanilines

Abstract

The oxidation of eight 3(or 6)-substituted-2-nitroanilines with iodosobenzene diacetate, in both benzene and acetic acid solution, has been investigated. Benzo-furazan oxides and azo compounds were produced in varying yields. Certain of these amines have also been oxidized with iodosobenzene diacetate in other solvents, and with sodium hypochlorite in ethanolic potassium hydroxide. Six of these 3(or 6)- substituted-2-nitroanilines have been oxidized with lead tetra-acetate, in both benzene and acetic acid solution, and varying yields of azo compounds were obtained. Benzaldehyde was isolated from the oxidation of benzylamine with iodosobenzene diacetate, in either benzene or acetic acid solution. The mechanisms of these reactions are discussed. New methods of synthesizing 6-methoxy-2-nitroaniline and 3-methoxy-2-nitroaniline are described.