Acetyl chloride → HCID 16779266, compound

Participants

Reaction Steps

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride (10.00 g, 46.8 mmol) was added portionwise into a mixture of acetone (75 mL) and 2N NaOH (75 mL). To this solution was added dropwise acetyl chloride (8.75 mL, 50 mmol) in acetone (50 mL) followed with 2N NaOH at room temperature. The reaction mixture was maintained at a pH>10 and stirred for 1 hour. The acetone was removed by evaporation under reduced pressure and acidified the residue by adding 3N HCl. The separated solid was collected by filtration, washed several times with water, and dried to give 2-(4-chlorobenzoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid as an enantiomeric mixture, 13.80 g (93.4%); mp 77-79° C.; 1H NMR (DMSO-d6) δ 2.92 (1H, dd, J=5.9 Hz and J=15.8 Hz, CH), 3.29 (1H, d, J=15.8 Hz, CH), 4.12 (1H, d, J=5.9 Hz, CH), 4.49 and 5.02 (each 1H, d, J=17.4 Hz, CH2), 7.09-7.17 (4H, m, 4×ArH), 7.40-7.58 (4H, m, 4×ArH); m/z 315.00 (M+H)+ Anal. Calcld. for C17H14ClNO3: C, 64.67; H, 4.47; N, 4.44. Found: C, 64.65; H, 4.46; N, 4.41.

Provenance & Evidence