反应详情

温度

70 °C

Iron (1.57 g, 28.2 mmol) and saturated aqueous ammonium chloride (11 mL) were added to a solution of 4-(3-methyl-5-nitrophenyl)-1-(2-methylallyl)-1H-pyrazole (2.42 g, 9.41 mmol) in ethanol (7 mL) and water (11 mL). The mixture was heated at 70° C. for 18 h, then allowed to cool to room temperature, passed through CELITE, washed with methanol, and concentrated under reduced pressure. The residue was diluted with EtOAc and washed with water, saturated aqueous sodium bicarbonate and brine. The organic layers were separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 3-methyl-5-(1-(2-methylallyl)-1H-pyrazol-4-yl)aniline. MS ESI calc'd. for C14H18N3 [M+H]+ 228. found 228. 1H NMR (500 MHz, DMSO-d6) δ 7.92 (s, 1H), 7.68 (s, 1H), 6.52 (s, 2H), 6.21 (s, 1H), 4.92 (s, 2H), 4.87 (s, 1H), 4.70 (s, 1H), 4.66 (s, 2H), 2.14 (s, 3H). 1.60 (s, 3H).

1. temperatureto cool to room temperature
2. washwashed with methanol
3. concentrationconcentrated under reduced pressure
4. additionThe residue was diluted with EtOAc
5. washwashed with water, saturated aqueous sodium bicarbonate and brine
6. customThe organic layers were separated
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure