Synthesis of 8-bromoisoquinolines and a crystal structure of an acyclic secondary amine-borane

Abstract

8-Bromo-7-methoxyisoquinoline was produced by Jackson's modification of the Pomeranz-Fritsch ring synthesis accompanied by 8-bromo-3-(8-bromo-7- methoxyisoquinolin-4-yl)-1,2,3,4-tetrahydro-7-methoxy-2-(4-methylphenylsulfonyl) isoquinoline. A mechanism for the formation of the latter is suggested. The ready formation of secondary amine-BH3 complexes was noted and the X-ray crystal structure of N-(2-bromo-3-methoxybenzyl)aminoacetaldehyde dimethyl acetal borane detailed.