Reinvestigation of bromination of 8-substituted quinolines and synthesis of novel phthalonitriles

Ökten S., Çakmak O., Saddiqa A., KESKİN B., Özdemir S., Inal M.

Organic Communications, vol.9, no.4, pp.82-93, 2016 (Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 9 Issue: 4
  • Publication Date: 2016
  • Journal Name: Organic Communications
  • Journal Indexes: Scopus
  • Page Numbers: pp.82-93
  • Keywords: Aminoquinoline, Bromination, Hydroxyquinoline, Methoxyquinoline, Phthalonitrile
  • Istanbul Gelisim University Affiliated: No

Abstract

© 2016 ACG Publications.Bromination of a series of 8-substituted quinolines was reinvestigated and specified for optimum yields and isolation conditions. Mono bromination of 8-hydroxyquinoline (2a) and 8-aminoquinoline (2c) gave mixture of mono and dibromo derivatives 5,7-dibromo-8-hydroxyquinoline (3a), 5,7-dibromo-8-aminoquinoline (3c), 7-bromo-8-hydroxyquinoline (3d), 5-bromo-8-aminoquinoline (3e) while 8-methoxyquinoline (2b) furnished 5-bromo-8-methoxyquinoline (3f) as sole product. Novel phthalonitriles, 4-(quinolin-8-yloxy)phthalonitrile (6) and 4-chloro-5-(quinolin-8-yloxy)phthalonitrile (8) of 8-hydroxyquinoline (2a) were synthesized and converted into their respective bromo derivatives 4-(5-bromoquinolin-8-yloxy)phthalonitrile (7) and 4-((5-bromoquinolin-8-yl)oxy)-5-chlorophthalonitrile (9).