HCID 86694134, compound → 7-Methoxy-1,2-dihydroquinolin-2-one

Participants

Reaction Steps

(E)-Ethyl 3-(4-methoxy-2-nitrophenyl)acrylate (20.00 g, 80 mmol) and iron powder (3.39 mL, 478 mmol) were mixed in acetic acid (300 mL). The reaction mixture was stirred at room temperature for 4 days. The reaction mixture was filtered through CELITE™. The filtrate was partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer was separated and extracted once more with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The resulting crude product was diluted with dichloromethane and filtered. The filtrate was diluted with hexanes and partially concentrated. The resulting precipitate was filtered off to yield 7-methoxyquinolin-2(1H)-one (13.16 g, 75 mmol, 94% yield) as a light yellow solid.

Provenance & Evidence