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Chemistry of Heterocyclic Compounds

, Volume 8, Issue 10, pp 1212–1215 | Cite as

Reaction of anthranilic acid and methoxy- and nitro-substituted anthranilic acid with p-toluenesulfonyl chloride in pyridine

  • M. V. Loseva
  • B. M. Bolotin
Article

Abstract

The reaction of anthranilic acid and methoxy- and nitro-substituted anthranilic acid with p-toluenesulfonyl chloride in pyridine was investigated. Anthranilic acid and its methoxy-substituted derivatives react to give the corresponding 2-(2-tosylaminophenyl)-4H-3,1-benzoxazin-4-ones and N,N'-ditosyldianthranilides. At 20°C, 4-nitroanthranilic acid gives primarily 2-(2-amino-4-nitrophenyl)-7-nitro-4H-3,1-benzoxazin-4-one, while its tosyl derivative is obtained at 114°. The products of the reaction of 5-nitroanthranilic acid with p-toluenesulfonyl chloride are 2-nitro-11H-pyrido[2,1-b]quinazolin-11-one and 2-(2-amino-5-nitrophenyl)-6-nitro-4H-3, 1-benzoxazin-4-one. The yield of benzoxazinone generally increases as the temperature is raised.

Keywords

Chloride Organic Chemistry Pyridine Methoxy Tosyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

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Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • M. V. Loseva
    • 1
  • B. M. Bolotin
    • 1
  1. 1.All-Union Scientific-Research Institute of Chemical Reagents and Especially Pure Chemical SubstancesMoscow

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