Acetyl chloride → 1-(5-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Participants

Reaction Steps

To a solution of the product of step (b) (6.26 g, 31.4 mmol) and triethylamine (9.6 ml, 69.0 mmol) in CH2Cl2 (150 ml) was added acetyl chloride (2.7 ml, 37.7 mmol) at 0° C. over a period of 15 min. The reaction mixture was stirred at room temperature for 18 h after which time the solution was washed sequentially with H2O and saturated aqueous sodium bicarbonate solution, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified on silica gel eluting with EtOAc to afford the subtitle compound as an orange oil (6.07 g, 94%). Rf 0.65 (CH2Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/s 206 (MH+).

Provenance & Evidence