Acetyl chloride → Acetyl chloride

Participants

Reaction Steps

To a round-bottomed flask containing 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol (88.15 g) was added dichloromethane (DCM, 600 mL) followed by triethylamine (38 mL, 270.8 mmol) and the solution was stirred for 5 minutes. In a separate flask a solution of acetyl chloride (14.4 mL, 202.5 mmol) in dichloromethane (300 mL) was prepared. The acetyl chloride solution was added to the reaction mixture in a dropwise fashion. The reaction was stirred at ambient temperature for 4 h. Additional acetyl chloride (2.8 mL in DCM (50 mL)) was added and the reaction mixture was stirred at ambient temperature overnight. At this time additional acetyl chloride (1.4 mL in dichloromethane (25 mL)) was added and the reaction was stirred at ambient temperature for 1 h. Additional dichloromethane (200 mL) was then added and the reaction was transferred to a separatory funnel. The organic layer was washed with water (2×800 mL) and brine (1×800 mL). The organic layer was separated, dried (MgSO4), filtered, and the solvent evaporated to afford 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propyl acetate (60.8 g) as a bright yellow solid.

Provenance & Evidence