3-chloro-N-(2-hydroxyphenyl)propanamide → 8-Hydroxy-3,4-dihydroquinolin-2(1h)-one

Participants

Reaction Steps

A mixture of 3-chloro-N-(2-hydroxyphenyl)propanamide (0.25 g, 1.25 mmol) and aluminium chloride (AlCl3) (0.5 g) was heated with stirring at 130–135° C. for 5 h. After cooling to room temperature, the reaction mixture was quenched with water (3 ml), and extracted with ethyl acetate (3×5 ml). Evaporation of the solvent and flash chromatography of the residue on silica gel with ethyl acetate/heptane (1:1) afforded colourless crystals of the subtitled compound (95 mg, 46.5%).

Provenance & Evidence