Water → 2-Acetyl-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl Chloride

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4,4-dimethyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone (D2) (0.5 g, 2.5 mmol) in dry dichloromethane (2 ml) was added over 15 minutes to an ice-cooled, stirred solution of chlorosulfonic acid (1.7 ml, 25 mmol) in dry dichloromethane (6 ml). After stirring the solution at 0° C. for 1 h, it was warmed to ambient temperature and stirred for a further 3 h. The solution was then carefully poured onto a mixture of ice (30 g) and water (30 ml) with stirring. The layers were separated and the aqueous layer was extracted with dichloromethane (30 ml). The combined organic layers were dried (MgSO4) and concentrated in vacuo to an oil which was stirred at room temperature for 15 minutes with diethyl ether (30 ml) to afford the title compound (D3) as a white solid (0.21 g, 27%), δH (CDCl3, rotamers observed)/ppm 1.33, 1.37 (6H, 2×s), 2.21, 2.24 (3H, 2×s), 3.47, 3.66 (2H, 2×s), 4.77, 4.88 (2H, 2×s), 7.55-7.62 (1H, m), 7.77-7.90 (2H, m).

Provenance & Evidence