3-chloro-N-(3-fluorophenyl)propanamide → Carbostyril, 3,4-dihydro-7-fluoro-

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Reaction Conditions

Reaction Steps

To the solid of 3-chloro-N-(3-fluorophenyl)propanamide (3 g, 14.88 mmol) was added AlCl3 (6.3 g, 0.047 mmol) and maintained with an inert atmosphere of nitrogen with stirring for 5 h at 120° C. The reaction was then quenched with ice-water, extracted with ethyl acetate (3×50 ml) and the organic layers were combined, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography with 4% ethyl acetate in petroleum ether to afford 7-fluoro-1,2,3,4-tetrahydroquinolin-2-one as a white solid (1.5 g, 61%).

Provenance & Evidence