Reacción #2849

Ecuación de reacción

NaHCO3

3-methyl-4-nitrobenzonitrile

SnCl2

→

title compound

Rendimiento 70.7%

4-Amino-3-methyl benzonitrile

Rendimiento 70.7%

Disolventes

EtOAc

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting solution is heated
2. 2
   Temperaturaat reflux
3. 3
   Temperaturathe solution is cooled to ambient temperatures
4. 4
   Filtraciónthe resulting mixture is filtered through Celite
5. 5
   OtroThe filtered solution is separated
6. 6
   SecadoThe organic layer is dried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

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.

Fuente