Dichloromethane → 2-(8-Fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamine

Participants

Reaction Steps

To a stirred solution of 8-fluoro-6-nitro-1,2,3,4-tetrahydroquinoline (670 mg, 3.42 mmol) in N,N-Dimethylformamide (15 ml), cooled to 0° C. was added sodium hydride, 60% (437 mg, 10.93 mmol) with vigorous stirring. When bubbling subsided, 2-chloro-N,N-dimethylethanamine hydrochloride (984 mg, 6.83 mmol) was added and the reaction mixture (dark red) was stirred at room temperature. After 2 h, no product was observed so the reaction was heated to 90° C. and stirred. After 1 h, TLC showed the reaction to be complete. The mixture was then cooled to room temperature, diluted with water and extracted with ethyl acetate (3×). The combined organics were then washed with 1:1 water:brine (2×), then brine (1×). The organic phase was dried, filtered and concentrated, then chromatographed in 0-10% (2M NH3 in methanol) in 1:1 ethyl acetate:dichloromethane, giving the desired 2-(8-fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamine (514 mg, 1.923 mmol, 56.3% yield). NMR (DMSO-d6) δ 7.77 (dd, J=15 Hz, 2.7 Hz, 1H); 7.72 (m, 1H); 3.55-3.48 (m, 2H); 3.43-3.39 (m, 2H); 2.78-2.74 (m, 2H), 2.49-2.44 (m, 2H); 2.16 (s, 6H); 1.88-1.79 (m, 2H). ESI-MS (m/z, %): 268 (MH+, 100); 223 (5).

Provenance & Evidence