Acetone → 2-Chloro-6-methoxyquinoline-3-methanol

Participants

Reaction Steps

To the mixture of 2-chloro-6-methoxy-3-quinolinecarbaldehyde (3.1 g, 14 mmol) and methanol (10 ml), sodium borohydride (530 mg, 14 mmol) was added at 0° C. (an outer temperature), and the obtained reaction mixture was stirred at the same temperature for 30 minutes. Acetone was added to the reaction mixture at the same temperature, followed by the addition of water and ethyl acetate at the same temperature. The organic layer was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (heptane:ethyl acetate=1:1), thereby obtaining the entitled compound (3.0 g, 98%).

Provenance & Evidence