Water → HCID 18317731, compound

Participants

Reaction Steps

To 7-(5-fluoro-2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one hydrochloride (2.13 g) were added water (20 ml), anhydrous potassium carbonate (1.5 g) and ethyl acetate (50 ml). The mixture was shaken, and the separated upper layer was concentrated under reduced pressure. The residue was dissolved in dichloromethane (15 ml), and to the solution was added dropwise a solution of 1M-boron tribromide-dichloromethane (21 ml), while stirring in ice-cooling bath. The bath was removed, and the mixture was stirred for 2 hours, and poured onto ice-water. To the mixture was added excess amount of sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified with silica gel column chromatography to give 7-(5-fluoro-2-hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.773 g).

Provenance & Evidence