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Chemistry of Heterocyclic Compounds

, Volume 15, Issue 4, pp 418–421 | Cite as

Conversion of the quinoline ring to an indole ring

  • K. M. Dyumaev
  • E. P. Popova
Article
  • 59 Downloads

Abstract

4-Nitro-3-hydroxyquinoline is readily converted to indole derivatives in aqueous alkaline and acetic acid media. The contraction of the quinoline ring to an indole ring under the conditions of mild methylation of 4-nitro-3-hydroxyquinoline in an aqueous alkaline medium proceeds through the formation of the N-methyl de rivative of 4-nitro-3-hydroxyquinoline and N-methyl-2-formyl-3-nitroindole. 3-Nitroindole is formed when 4-nitro-3-hydroxyquinoline is heated in aqueous alkali, whereas isatin is formed in acetic acid. The methylation of 4-nitro-3-hydroxyquinoline in refluxing acetic acid leads to N-methylisatin.

Keywords

Methylation Acetic Acetic Acid Organic Chemistry Indole 
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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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • K. M. Dyumaev
    • 1
  • E. P. Popova
    • 1
  1. 1.Scientific-Research Institute of Organic Intermediates and DyesMoscow

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