Tetrahydrofuran → 2-(8-Fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamine
Reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[CH:12][C:13]=2[F:15])[CH2:8][CH2:7][C:6]1=O.C1COCC1>>[F:15][C:13]1[CH:12]=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=[C:9]2[C:14]=1[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:20])[CH2:6][CH2:7][CH2:8]2Participants
3
Conditions
- Temperature
- 0 °C
Procedure
1-(2-(Dimethylamino)ethyl)-8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (600 mg, 2.13 mmol) was added to a round bottom flask equipped with a stir bar. The flask was sealed and purged with argon. Borane.THF (1M solution in THF, 21.3 mL, 21.3 mmol) was added to the starting material and stirred to dissolve. The reaction mixture was heated to reflux overnight. The reaction was cooled to 0° C. and then quenched with methanol (20 mL). The mixture was then concentrated in vacuo, redissolved in methanol and refluxed for 4 h. The mixture was then concentrated onto silica gel and chromatographed using 0-10% (2M NH3 in MeOH) in dichloromethane. Yield: 364 mg, 64%. 1H NMR (CDCl3) δ 1.95 (m, 2H), 2.27 (s, 6H), 2.56 (m, 2H), 2.77 (m, 2H), 3.41 (m, 4H), 7.69 (m, 1H), 7.77 (dd, 1H, J=9 Hz, 2.7 Hz). EI-MS: 58 (100).