Title

Synthesis and characterization of 4'-amino and 4'-nitro derivatives of 4-N, N-dimethylaminotriphenylmethane as precursors for a proximate malachite green metabolite

Document Type

Article

Date of Original Version

9-15-2000

Abstract

This paper describes the preparation of 4'-amino (2) and 4'-nitro (3) derivatives of 4-N, N-dimethylaminotriphenylmethane as precursors for presumed DNA-binding metabolites of malachite green. The primary amine 2 was synthesized via a condensation of 4-lithiated bis-(N, N-trimethylsilyl)aniline and 4-(dimethylamino)benzophenone. A simple nitro-dediazoniation reaction of 2 failed to afford 3, but gave exclusively a mixture derived from hydro-dediazoniation followed by nitration and N-dealkylative-N-nitrosation. Direct nitration of N, N-dimethylaminotriphenylmethane, however, afforded 3 as well as other nitro isomers.

Publication Title

Tetrahedron

Volume

56

Issue

38

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