HCID 21447050, compound → HCID 21447048, compound

Participants

Reaction Steps

A mixture of 1-(2'-nitro-4'-methoxy-5'-bromobenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (3c) (850 mg) in absolute methanol (80 ml) containing palladium-charcoal catalyst (5%, 250 mg) was stirred under hydrogen until absorption ceased (approximately 6-8 hours). The catalyst was filtered, washed with methanol and the filtrate evaporated to give an oil which was crystallized from acetone to give white crystals of 1-(2'-amino-4'-methoxybenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (4f) (735 mg, 81%), mp 136°-137.5°. An analytical sample was prepared by recrystallization from acetone, mp 137.5°-138°; nmr δ (CDCl3), 2.05 (s, 6H, acetone CH3COCH3), 2.78 (s, 3H, NCH3), 3.88 and 3.92 (2s, 6H, 2OCH3), and 5.94-6.57 (CM, 5H, aromatic H).

Provenance & Evidence