Summary
From the product of the benzanthrone condensation on 2-chloroanthraquinone 4-chlorobenzanthrone, identical with the substance obtained by the Sandmeyer reaction on 4-aminobenzanthrone, has been isolated. Chromatographic analysis of a benzene solution of the residue on alumina gave 9-chlorobenzanthrone. The residue after separation of 9-chlorobenzanthrone contains the 10-isomer. 2-Chloroanthraquinone-1-carboxylic acid, prepared by chromic acid oxidation of 4-chlorobenzanthrone, has m.p. 280–81°, and not 176–77°, as stated in the literature. For comparison with the anthraquinone carboxylic acids obtained by oxidation of chlorobenzanthrones, 3-chloroanthraquinone-1-carboxylic acid has been prepared from 1-amino-3-chloroanthraquinonevia 3-chloro-1-cyanoanthraquinone. There is no evidence of the formation of the unknown 5-chlorobenzanthrone in the product of the benzanthrone condensation on 2-chloroanthraquinone.
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Pandit, P.N., Tilak, B.D. & Venkataraman, K. Anthraquinone and anthrone series. Proc. Indian Acad. Sci. (Math. Sci.) 38, 355–360 (1953). https://doi.org/10.1007/BF03045243
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DOI: https://doi.org/10.1007/BF03045243