反応 #599897

反応方程式

acetic anhydride

ethyl acetate

3-chloro-1(pyridin-3-yl)-1H-pyrazol-4-amine

ethyl acetate

sodium bicarbonate

→

desired product

収率 66.0%

N-(3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide

収率 66.0%

溶媒

water

反応条件

後処理

1. 1
   その他to afford a suspension
2. 2
   ろ過the resulting suspension was filtered
3. 3
   洗浄The solid was rinsed with water (10 mL)
4. 4
   その他The solid was further dried under vacuum at 20° C.

実験手順

A 100 mL three-neck round bottom flask was charged with 3-chloro-1(pyridin-3-yl)-1H-pyrazol-4-amine (1.00 g, 5.14 mmol) and ethyl acetate (10 mL). sodium bicarbonate (1.08 g, 12.9 mmol) was added, followed by dropwise addition of acetic anhydride (0.629 g, 6.17 mmol) at <20° C. The reaction was stirred at 20° C. for 2 hours to afford a suspension, at which point thin layer chromatography analysis [Eluent: ethyl acetate] indicated that the reaction was complete. The reaction was diluted with water (50 mL) and the resulting suspension was filtered. The solid was rinsed with water (10 mL) followed by methanol (5 mL). The solid was further dried under vacuum at 20° C. to afford the desired product as a white solid (0.804 g, 66%): mp 169-172° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.84 (s, 1H), 9.05 (dd, J=2.8, 0.8 Hz, 1H), 8.82 (s, 1H), 8.54 (dd, J=4.7, 1.4 Hz, 1H), 8.20 (ddd, J=8.4, 2.8, 1.4 Hz, 1H), 7.54, (ddd, J=8.3, 4.7, 0.8 Hz, 1H), 2.11 (s, 3H); 13C NMR (101 MHz, DMSO-d6) δ 168.12, 147.46, 139.42, 135.46, 133.60, 125.47, 124.21, 122.21, 120.16, 22.62; EIMS m/z 236 ([M]+).

出典