The aluminium chloride-catalysed decomposition of some N-(3-bromopropyl)arylamines

Abstract

N-(3-Bromopropyl)aniline hydrobromides were decomposed in decalin in the presence of anhydrous aluminium chloride to give high yields of the corresponding tetrahydroquinolines. The reaction has been extended to the corresponding salts of N-(3-bromopropyl)tetrahydroquinoline and N-(3-bromopropyl)indoline to give julolidine and lilolidine, respectively. The utility of the method has been illustrated by the preparation of 5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3,2,1-jk]carbazole and 2,3,7a,8,9,10,11,11a-octahydro-1H,7H-pyrido[3,2,1-de]acridine.