Water → 1,2,3,4-Tetrahydro-1-methylquinoline

Participants

Reaction Steps

1,2,3,4-Tetrahydroquinoline (6.66 g, 50 mmol) was added to 40 ml of water, 40 ml of ethyl acetate, and 5.04 g (60 mmol) of sodium bicarbonate to which was added 5.68 ml (60 mmol) of dimethylsulfate dropwise. The reaction was stirred at room temperature for 21/2 hours, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate, then the organic layers were combined and evaporated to give 4.56 g (62% yield) of the title compound. NMR (CDCl3) δ 1.93 (quintet, 2, CH2), 2.74 (tr, 2, CH2), 2.81 (s, 3, NMe), 3.17 (tr, 2, CH2), 6.55 (m, 2, Ar), 6.97 (m, 2, Ar).

Provenance & Evidence