Water → HCID 11797413, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetate (5.8 g) in tetrahydrofuran (100 ml) was added dropwise to a suspension of lithium aluminium hydride (0.455 g) in tetrahydrofuran (50 ml) at 0° C. After stirring the reaction mixture at 0° C. for 1 hour, water (2.5 ml) was added dropwise, and the mixture was stirred for additional 30 minutes. The insoluble solid was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (1/1, v/v) gave ethyl 2-(2-hydroxyethyl)-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (1.75 g, 33%) which was then recrystallized from ethyl acetate-hexane. Colorless prisms. mp. 150°-151° C.

Provenance & Evidence