Ethyl Acrylate → (E)-ethyl 3-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)acrylate

Participants

Reaction Steps

To a stirred solution of 6-bromo-1-(4-methoxybenzyl)quinolin-2(1H)-one (1 g, 2.9 mmol) in DMF (10 mL) were added potassium carbonate (1.19 g, 8.69 mmol), n-tert butyl ammonium chloride (0.66 g, 2.9 mmol), ethyl acrylate (1.16 g, 11.6 mmol) and palladium acetate (0.65 g, 2.9 mmol). The reaction mixture was stirred at room temperature for 20 min, then heated to 120° C. overnight. The reaction mixture was concentrated. To this, was added water and extracted with ethyl acetate, and the combined organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give (E)-ethyl 3-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)acrylate as a white solid (0.8 g, 80%).

Provenance & Evidence