Reaktion #2850

Reaktionsgleichung

4-amino-3-methyl benzonitrile

benzophenone

p-toluenesulfonic acid

→

title compound

Ausbeute 90.3%

4-(Benzhydrylidene-amino)-3-methyl-benzonitrile

Ausbeute 90.3%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction vessel is fitted with a Dean-Stark trap
2. 2
   Temperaturthe solution is heated
3. 3
   Temperaturat reflux
4. 4
   Temperaturthe solution is cooled to ambient temperatures
5. 5
   EinengenThe solution is concentrated
6. 6
   SonstigeThe crude material is purified by column chromatography
7. 7
   Wascheneluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes

Vorschrift

To a solution of 4-amino-3-methyl benzonitrile (1.20 g, 9.08 mmol) in 75 mL of toluene is added benzophenone (1.74 g, 9.53 mmol) and p-toluenesulfonic acid (0.43 g, 2.1 mmol). The reaction vessel is fitted with a Dean-Stark trap and the solution is heated at reflux. After 24 h, the solution is cooled to ambient temperatures. The solution is concentrated. The crude material is purified by column chromatography eluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound (2.43 g, 8.2 mmol) is obtained as an oil.

Quelle