Water → alpha-Phenyl-2-pyridineacetonitrile

Participants

Reaction Steps

To a solution of benzyl cyanide (5.00 g, 42.7 mmol) and 2-chloropyridine (4.85 g, 42.7 mmol) in 15 ml of toluene was added finely powdered sodium amide (3.33 g, 85.4 mmol) in portions keeping the temperature between 20-30° C. The suspension was refluxed for 6 h. After cooling, 100 ml water is added and the product is worked up with ethyl acetate/water. After drying (MgSO4) and concentration, the crude material is purified by flash chromatography on silicagel using a 1:4 mixture of ethyl acetate and hexane as eluant to yield 3.40 g (17.5 mmol, 41%) of (RS)-phenyl-pyridin-2-yl-acetonitrile as a white solid, m.p. 89° C. and MS: m/e=194 (M+).

Provenance & Evidence