Chloroacetyl chloride → 2-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one

Participants

Reaction Steps

To a solution of 1,2,3,4-tetrahydroquinoline (3, 2.00 g, 15.0 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added chloroacetyl chloride (1.80 g, 16.0 mmol) followed by dropwise addition of Et3N (2.50 mL, 18.0 mmol). The reaction was stirred overnight under N2. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with 5% HCl (15 mL), water (2×15 mL), and saturated NaCl (15 mL). Dried over MgSO4, filtered, and concentrated to give 3.05 g of 4. This crude material was used in subsequent reactions without further purification.

Provenance & Evidence