The preparation and oxidative dimerisation of 2‐acetyl‐7‐hydroxy‐1,2,3,4‐tetrahydroisoquinoline. A new approach to tetrahydroisoquinoline synthesis

Abstract The title compound has been prepared from 1,2,3,4‐tetrahydroisoquinoline via successive nitration, acet‐ylation, reduction and diazotisation. Earlier conflicting reports on the nitration of tetrahydroisoquinoline have been clarified. A better synthetic route, based upon reduction of the corresponding isocarbostyril, has been devised and should be applicable to the obtention of a wide range of tetrahydroisoquinolines. The structure of the neutral product of oxidative dimerisation of 2‐acetyl‐7‐hydroxy‐1,2,3,4‐tetrahydroisoquinoline has been established.