Acetic Acid → 2-(2-(4-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)-2H-tetrazol-5-yl)-4,5-dimethoxyaniline(WXC04283)

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Reaction Conditions

Reaction Steps

Iron (433 g, 7.76 mol) and 5.4 L of 50% aqueous acetic acid were added to a reactor, and stirred for 1 hour at 80° C. 2-(4-(5-(4,5-dimethoxy-2-nitrophenyl)-2H-tetrazol-2-yl)phenethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1.06 kg, 1.94 mol) obtained in Step 4 was slowly added thereto for two hours, followed by stirring for 1 hour. After checking completion of the reaction by thin layer chromatography (eluent: chloroform/methanol=15/1), the reactor was cooled to room temperature. 5.3 L of chloroform and 2.4 L of water were added thereto and the resulting mixture was filtered through a Celite pad. The organic layer was collected, 6.6 L of saturated sodium bicarbonate solution was slowly added thereto with stirring. The organic layer was collected, and the aqueous layer was further extracted using 1.25 L of chloroform. The resulting organic layer was dried over magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was mixed with 10.6 L of methanol, followed by stirring. The resulting mixture was filtered, and dried with hot air at 40° C. in an oven to obtain the title compound (0.87 kg, 87%).

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