A rapid and simple synthesis of reactive metabolites of carcinogenic aromatic amines in high yield

Abstract

Reactive metabolities of carcinogenic aromatic amines can be obtained by partial reduction of the corresponding nitroarenes with Pd/C and hydrazine hydrate. Using an excess of hydrazine at 0–5°C in tetrahydro-furan, bicyclic aromatic nitro compounds are converted into the corresponding hydroxylamines. Further reduction to the amines is very slow under these conditions. A series of arylbydroxamic acids was synthesized in good yields by adding acetyl chloride to the reaction mixture, followed by alkaline hydrolysis of the O-acetyl moiety.