Potassium Carbonate → 5-chloro-6,7-bis((4-methoxybenzyl)oxy)-3,4-dihydroisoquinolin-1(2H)-one

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To the solution of 5-chloro-6,7-dihydroxy-3,4-dihydroisoquinolin-1(2H)-one (0.619 g, 2.9 mmol) in N,N-dimethylformamide (DMF) (10 mL) was added potassium carbonate (1.202 g, 8.70 mmol) followed by 1-(chloromethyl)-4-methoxybenzene (0.767 mL, 5.66 mmol). Stirred at room temperature for 4 hours. The mixture was extracted with ethyl acetate, washed with water, sodium chloride, and dried over magnesium sulfate. The crude mixture was chromotagraphed on silica ISCO column to give 5-chloro-6,7-bis((4-methoxybenzyl)oxy)-3,4-dihydroisoquinolin-1(2H)-one (1.017 g, 2.241 mmol, 77% yield). LCMS (M+H)+: 454.4

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