A New Synthesis of 2 : 7-Disubstituted-1 : 2 : 3 : 4-tetrahydro-iso-quinolines

IT has been shown by Holliman and Mann1that o-2-bromoethyl-benzyl bromide (I) condenses readily with primary amines to give 2-substituted-1 : 2 : 3 : 4-tetrahydro-iso-quinolines (II). Although hitherto this has apparently been the only known method for the synthesis of 2-aryl-iso-quinolines of type (II), it has one serious disadvantage, namely, that for various reasons it does not lend itself to the preparation of iso-quinolines of this type having substituent groups in the benzene ring. The presence of such groups may be essential if the tetrahydro-iso-quinoline is to possess marked physiological action. To overcome this difficulty we have developed the following synthesis.