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

Salih Ökten, Osman Çakmak, Aisha Saddiqa, Bahadır Keskin, Seda Özdemir and Merve İnal

Department of Mathematic and Science Education, Faculty of Education, Kırıkkale University, 71450, Yahşihan, Kırıkkale, Türkiye

Department of Nutrition and Dietetics, School of Health Sciences, İstanbul Gelişim University, 34315 Avcılar, İstanbul, Türkiye

Department of Chemistry, Faculty of Natural Sciences, Government College Women University, 51310, Sialkot, Pakistan

Department of Chemistry, Faculty of Art and Science, Yıldız Technical University, 34210, Davutpaşa, İstanbul, Türkiye

Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University, 60240, Tokat, Türkiye

Abstract: 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-methoxy quinoline ( 2b ) furnished 5-bromo-8-methoxyquinoline ( 3f) as sole product. N ovel phthalonitrile s, 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) and4-((5-bromoquinolin-8-yl)oxy)-5-chlorophthalonitrile (9) .

Keywords : Bromination ; hydroxyquinoline ; phthalonitrile ; methoxyquinoline; aminoquinoline. © 2016 ACG Publications. All rights reserved.