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-tetrahydroquinolin (3) (2.00 g, 15.0 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added chloroacetyl chloride (1.27 mL, 16.0 mmol) followed by drop wise addition of triethylamine (2.50 mL, 18.03 mmol). The reaction was stirred overnight under N2. The reaction mixture was then diluted with CH2Cl2 (50 mL), washed with 5% HCl (15 mL), H2O (2×15 mL) and brine. 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