Syntheses of Deuterated 3'-Hydroxymethyl-4- (dimethylamino) -azobenzene and Related Compound

Abstract

3'-Hydroxymethyl-4- (dimethylamino) azobenzene (I), a new potent hepatocarcinogen, and 3, 3'-bis (hydroxymethyl) azobenzene (II) were labeled with multiple-deuterium for the purpose of investigating their metabolisms by the ion cluster technique. I-d₄ was obtained in a 22% yield from benzoic-d₅ acid (99 atom% D) by nitration, catalytic hydrogenation, reduction, and coupling of the diazonium salt with N, N-dimethylaniline and its deuterium content was 99 atom%. On the other hand, II-d₈ was obtained in a 7% yield from 3-nitrobenzoic-d₄ acid by reduction and was 91 atom% D.