2-Methoxyethylamine → N,N-diethyl-4-[(2-methoxyethyl)amino]-3-nitrobenzamide
反応式
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[CH3:18][O:19][CH2:20][CH2:21][NH2:22]>CCO>[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:22][CH2:21][CH2:20][O:19][CH3:18])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2]参加物
4
反応条件
- 温度
- 90 °C
実験手順
Following general procedure 2B: A mixture of N,N-diethyl-4-fluoro-3-nitrobenzamide (0.200 g, 0.833 mmol), 2-methoxyethanamine (0.065 mL, 0.757 mmol) in 80% aq. EtOH (5 mL) was heated at 90° C. overnight: After work-up, the crude product was purified by silica gel column chromatography (33% EtOAc/Hexanes to 50% EtOAc/Hexanes) to provide the title compound (0.191 g, 85%) as a bright yellow solid. 1H-NMR (CDCl3): δ 8.34 (s, 1H), 8.28 (d, J=2.8 Hz, 1H), 7.56 (dd, J=8.4 Hz, J=1.6 Hz, 1H), 6.91 (d, J=9.2 Hz, 1H), 3.69 (t, J=5.6 Hz, 2H), 3.53 (q, J=5.6 Hz, 2H), 3.44 (s overlapping with br s, 7H), 1.22 (t, J=6.4 Hz, 6H). MS (ESI) (M+H)+=296