Phosphorus trichloride → N-(4-Methoxybenzyl)-4-nitropyridin-2-amine
反応式
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9]2[N+:10]([O-])=[CH:11][CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][N:10]=2)=[CH:19][CH:20]=1参加物
4
反応条件
- 温度
- 0 °C
実験手順
To a 2 L 3 neck round bottom flask fitted with a mechanical stirrer, was added N-(4-methoxybenzyl)-4-nitropyridin-2-amine 1-oxide (38.72 g, 0.14 mol) and chloroform (580 mL). The reaction mixture was cooled to 0° C. and phosphorus trichloride (36.8 mL, 0.42 mol) was added dropwise. The reaction mixture was allowed to warm to rt and stir overnight. The reaction mixture was filtered and the resulting solid was slurried with hexanes and filtered (repeated several times) to afford N-(4-methoxybenzyl)-4-nitropyridin-2-amine (39.34 g, 102%) as a yellow solid. LCMS: (FA) ES+ 260; 1H NMR (400 MHz, CD3OD) δ ppm 8.20 (d, J=5.9 Hz, 1H), 7.33-7.25 (m, 1H), 7.22 (dd, J=5.9, 2.0 Hz, 1H), 6.89 (d, J=8.7 Hz, 1H), 4.51 (s, 1H), 3.77 (s, 1H).