Benzonitrile → 2-Amino-2-phenylacetonitrile

Participants

Reaction Conditions

Reaction Steps

10 millimoles (1.031 g) of benzonitrile are dissolved in 10 ml of anhydrous toluene at 0° C., under an argon atmosphere. 15 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (10 ml) are added dropwise, at this temperature. The reaction mixture is maintained at 0° C. for 1 hour, then 2 ml (1.5 eq) of trimethylsilyl cyanide are added. The stirring is maintained for 3 hours at room temperature, then the mixture is hydrolyzed with 10 ml of methanol, then with pasty sodium sulfate. After purification of α-aminonitrile by an acid-base extraction there are obtained 0.820 g of 2-amino-2-phenyl-acetonitrile, with a yield of 62%.

Provenance & Evidence