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Azo pigments and their intermediates. A facile synthesis of photoreceptor grade anilide couplers from 2-hydroxy-11H-benzo(a)carbazole-3-carboxylic acid

Authors
Journal
Dyes and Pigments
0143-7208
Publisher
Elsevier
Publication Date
Volume
21
Issue
2
Identifiers
DOI: 10.1016/0143-7208(93)85017-t

Abstract

Abstract A facile, two-step synthesis for anilide couplers of 2-hydroxy-11H-benzo(a) carbazole-3-carboxylic acid, by first converting the acid to its phenyl ester and then condensing the phenyl ester with an aniline derivative to form an anilide, is reported. The synthesis is very general and a variety of anilides have been synthesized in an overall yield of⩾60%. The synthesized anilides are of high purity and can be used to synthesize photoreceptor-grade (IR-sensitive) azo pigments without further purification. The procedure described in this work is shown to be more efficient than other processes reported in the literature, such as direct condensation of the acid with an aniline or indirect condensation of the acid with an aniline through an acid chloride or methyl ester intermediate. More importantly, we have demonstrated that neither yield-loss nor deterioration in product purity is observed as the scale of the synthesis increases.

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