Studies of N-hydroxy-4-aminoazo dyes. I. Syntheis of N-hydroxy-N-methyl-4-aminoazo dyes and the acyl derivatives, and their degradation in alkaline solution.

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Alkaline hydrolysis of N-benzoyloxy-N-methyl-4-aminoazobenzene (II) in the presence of ascorbic acid gave N-hydroxy-N-methyl-4-aminoazobenzene (I) which has been estimated as proximate compound of hepatocarcinogenic N-methyl-or N, N-dimethyl-4-aminoazobenzene. Several acyl derivatives of I including acetyl derivative were synthesized. Alkaline treatment of I or II in the presence of dissolved oxygen, yield 4-nitroazobenzene (IV) and 4, 4′-bisphenylazo-azoxybenzene (V), probably through intermediate forms, nitron and hydroxylamine compound.

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