Acetic Acid → HCID 10640530, compound

Participants

Reaction Steps

A solution of 8-methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one (1.2 g, 5.2 mmol) and 4-methylbenzaldehyde (0.68 g, 5.7 mmol) in 20 mL of tetrahydrofuran and 7 mL of 1,3-dimethyl-2-imidazolidinone is treated with glacial acetic acid (0.29 mL, 5.2 mmol). The mixture is stirred for 10 minutes, and then sodium triacetoxyborohydride (1.6 g, 7.5 mmol) is added in portions over 30 minutes. The mixture is stirred for 16 hours, then added to 300 mL of ice water. The precipitated solid is filtered, washed with water, and recrystallized from ethyl acetate to yield 1.2 g (70%) of product, mp 147°-149° C.

Provenance & Evidence