Abnormal products of the Pschorr reaction of 8-amino-1,2,3,4-tetrahydro-1-phenethylisoquinoline
Abstract
The thermal decomposition of the diazonium salt from 8-amino-1,2,3,4-tetrahydro-6,7-dimethoxy-1-(4-methoxyphenethyl)-2-methylisoquinoline (X) gave a mixture of anisaldehyde (XXI), 1,2,3,4-tetrahydro-6,7-dimethoxy-1-[β-hydroxy-β-(4-methoxyphenyl)ethyl]-2-methylisoquinoline (XXIIa) and its diastereoisomer (XXIIb). On the other hand, the treatment of the diazonium salt with hypophosphorous acid afforded 4-methoxystyrene (XXVI), (XXIIa), (XXIIb), and a deamination product (XVII).