Abstract
The Bischler-Napieralski cyclization of phenethylamide (VII), having an ethoxycarbamido group in the 3-position of the benzene ring was found to take place in the positions para and ortho to the ethoxycarbamido group, and the two isoquinoline derivatives could be separated in the stage of N-methyl-1, 2, 3, 4-tetrahydroisoquinolines (Xa and Xb) in 1 : 3.5 ratio (para to ortho). Deamination of the 8-amino compound (XIb) gave a mixture of 6, 7-dimethoxy derivative (XIb) and dl-nuciferin (XIIc), which were separated by chromatography on silica gel to give two components in 2 : 1 ratio.
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