HCID 21447071, compound → HCID 21447044, compound

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Reaction Steps

A mixture of the 1-(2'-methoxy-6'-nitrobenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (3b) (1 g) and 5% palladium-charcoal (0.2 g) in absolute ethanol (150 ml) was shaken with hydrogen at room temperature and atmospheric pressure overnight (19 hours). The mixture was filtered through celite, and the filtrate was evaporated to dryness to leave a transparent brown oil. This crystallized from methanol-ether to give 1-(2'-amino-6'-methoxybenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline (4b) (0.885 g, 93%), mp 158°-160°. Recrystallization from absolute ethanol gave feathery needles, mp 161°-162°; λmaxKBr 2.88 and 2.96 μ (OH and NH2); λmaxEtOH (c) 285.5 nm (5480); nmr τ 3.02-3.87 (5H, aromatic H), 6.24 (6H, s, O--CH3), and 7.66 (3H, s, N--CH3); mass spectrum m/e 327 (M+ - 1), 296, 205, 192, 177, and 148.

Provenance & Evidence