反応 #2849

反応方程式

NaHCO3

3-methyl-4-nitrobenzonitrile

SnCl2

→

title compound

収率 70.7%

4-Amino-3-methyl benzonitrile

収率 70.7%

溶媒

EtOAc

EtOH

反応条件

後処理

1. 1
   温度The resulting solution is heated
2. 2
   温度at reflux
3. 3
   温度the solution is cooled to ambient temperatures
4. 4
   ろ過the resulting mixture is filtered through Celite
5. 5
   その他The filtered solution is separated
6. 6
   乾燥The organic layer is dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.3 mmol) in 100 mL of EtOH is added SnCl2 (13.9 g, 61.7 mmol). The resulting solution is heated at reflux. After 2 h, the solution is cooled to ambient temperatures. The solution is poured into 150 mL of ice water. The pH of the solution is adjusted to >7 with a solution of saturated NaHCO3. The solution is diluted with EtOAc and the resulting mixture is filtered through Celite. The filtered solution is separated. The organic layer is dried over MgSO4, filtered and concentrated to give the title compound (1.57 g, 8.7 mmol) as an off-white solid.

出典