Carbon Tetrachloride → (R)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of acetic acid (R)-2-(5-amino-1-oxo-1H-isoquinolin-2-yl)-propyl ester (20 g, 0.07 mol) in carbon tetrachloride (400 mL, 4 mol) at 60° C. was added a solution of N-chlorosuccinimide (11 g, 0.082 mol) in N,N-dimethylformamide (140 mL, 1.8 mol) in 50 minutes. The mixture was stirred at 60° C. for an additional 15 minutes. The cooled mixture was diluted with dichloromethane (400 mL), washed with sodium bicarbonate (100 mL×3), and concentrated under reduced pressure. The mixture was purified by flash chromatography to afford the desired product as a brown oil.

Provenance & Evidence