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Anthraquinone and anthrone series

Part XIII. Synthesis of 5-substituted benzanthrones

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Summary

5-Nitrobenzanthrone has been synthesized by nitration of 4-acetamidobenzanthrone, hydrolysis to 4-amino-5-nitrobenzanthrone and subsequent deamination. The adjacent orientation of the amino and nitro groups was shown by reduction to a diamine, which formed a quinoxaline with phenanthraquinone and an imidazole with benzoyl chloride. Reduction of 5-nitrobenzanthrone gave 5-aminobenzanthrone which was converted to 5-chlorobenzanthrone. Oxidation of 5-chlorobenzanthrone gave 3-chloroanthraquinone-1-carboxylic acid, identical with the acid prepared from 1-amino-3-chloroanthraquinone.

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Authors and Affiliations

  1. Department of Chemical Technology, University of Bombay, India

    S. S. Malhotra, B. D. Tilak F.A.Sc. & K. Venkataraman F.A.Sc.

Authors
  1. S. S. Malhotra
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  2. B. D. Tilak F.A.Sc.
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  3. K. Venkataraman F.A.Sc.
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Malhotra, S.S., Tilak, B.D. & Venkataraman, K. Anthraquinone and anthrone series. Proc. Indian Acad. Sci. (Math. Sci.) 38, 361–366 (1953). https://doi.org/10.1007/BF03045244

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  • DOI: https://doi.org/10.1007/BF03045244

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