Reaktion #2849

Reaktionsgleichung

NaHCO3

3-methyl-4-nitrobenzonitrile

SnCl2

→

title compound

Ausbeute 70.7%

4-Amino-3-methyl benzonitrile

Ausbeute 70.7%

Lösungsmittel

EtOAc

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting solution is heated
2. 2
   Temperaturat reflux
3. 3
   Temperaturthe solution is cooled to ambient temperatures
4. 4
   Filtrationthe resulting mixture is filtered through Celite
5. 5
   SonstigeThe filtered solution is separated
6. 6
   TrocknenThe organic layer is dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

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.

Quelle