| Abstract: | The halogenation of 1,2,3,4-tetrahydrobenzoh]quinoline and of 3-hydroxy-1,2,3,4-tetrahydrobenzoh]quinoline and its O-benzoyl and N,O-dibenzoyl derivatives has been studied. The action of thionyl chloride or bromide on 1,2,3,4-tetrahydrobenzoh]quinoline at room temperature gives 6-chloro-1,2,3,4-tetrahydrobenzoh]quinoline and 6-bromo-1,2,3,4-tetrahydrobenzoh]quinoline. When 6-chloro-3-hydroxy-1,2,3,4-tetrahydrobenzoh]quinoline is heated with thionyl chloride, aromatization of the tetrahydropyridine ring takes place, and when 6-bromo-3-hydroxy-1,2,3,4-tetrahydrobenzoh]quinoline is heated with thionyl chloride, in addition to the aromatization of the tetrahydropyridine ring the bromine atom is replaced by a chlorine atom with the formation of 6-chlorobenzoh]quinoline. 6-Bromobenzoh]quinolme has been obtained by heating 3-hydroxy-1,2,3,4-tetrahydrobenzoh]quinoline with thionyl bromide.For Communication IV, see 6].Translated from Khimiya Geterotsiklicheskikh Soedinenii.Vol. 6,No.7, pp. 969–973, July, 1970. |
