Reaction #2850

Reaction equation

4-amino-3-methyl benzonitrile

benzophenone

p-toluenesulfonic acid

→

title compound

Yield 90.3%

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

Yield 90.3%

Solvents

toluene

Conditions

Workup

1. 1
   OtherThe reaction vessel is fitted with a Dean-Stark trap
2. 2
   Temperaturethe solution is heated
3. 3
   Temperatureat reflux
4. 4
   Temperaturethe solution is cooled to ambient temperatures
5. 5
   ConcentrationThe solution is concentrated
6. 6
   OtherThe crude material is purified by column chromatography
7. 7
   Washeluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes

Procedure

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.

Source