Water → HCID 11797413, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3-ethoxycarbonylquinoline-2-acetate (5.8 g) in tetrahydrofuran (100 ml) was added dropwise to a suspension of lithium aluminum hydride (0.455 g) in tetrahydrofuran (50 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour, and then water (2.5 ml) was added dropwise, and the mixture was stirred for 30 minutes. The insoluble solids were separated by filtration, 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 4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinoline-3-carboxylate (1.75 g, 33%). This was recrystallized from ethyl acetate-hexane. Colorless prisms, mp. 150°-151° C.

Provenance & Evidence