Sodium Hydroxide → HCID 14625300, compound

Participants

Reaction Steps

N-(1-[6-benzyloxy-7-methoxy-1,2,3,4-tetrahydroisoquinol-2-yl]ethylidene)-2-cyano-4,5-dimethoxyaniline (10.92 g), anhydrous zinc chloride (3.16 g) and dimethylacetamide (25 ml) were mixed at 20° and then stirred at reflux for two hours. The reaction mixture was allowed to cool to about 40° and then 2N sodium hydroxide (16 ml) was added. The mixture was cooled to 25° and stirred for fifteen mixtures. 2N Sodium hydroxide (10 ml) and water (50 ml) were added and the reaction mixture was then extracted with methylene chloride (3×100 ml). The combined organic extracts were washed (H2O), dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica (Merck "Art.9385") under medium pressure eluting with methylene chloride containing gradually increasing amounts (1-20%) of methanol. The combined product-containing fractions were evaporated and the residue was recrystallised from ethanol and washed (Et2O) to give 4-amino-2-(6-benzyloxy-7-methoxy-1,2,3,4-tetrahydroisoquinol-2-yl)-6,7-dimethoxyquinoline (7.1 g) as a pale yellow powder, m.p. 181°-2°.

Provenance & Evidence