Acetonitrile → 3-(Pyridin-3-yl)propanenitrile

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Reaction Steps

3-(3-Pyridinyl)propionitrile is prepared in this example. A three-neck flask carrying a magnetic stir bar is fitted with a thermometer, pressure equalizing addition funnel, and a reflux condenser carrying an argon inlet. Freshly powdered potassium hydroxide (6.6 g, 0.1 mol) and anhydrous acetonitrile (150 ml) are charged into the flask and heated at reflux while 3-pyridinecarboxaldehyde (10.7 g, 0.1 mol) in anhydrous acetonitrile (50 ml) is added dropwise over a period of about five minutes and refluxing continued for about another three minutes. The resulting hot reaction mixture is poured into an ice/water mixture (100 g), and the resulting solution is extracted with CH2Cl2 (3×100 ml), dried with Na2SO4, and evaporated to give crude 3-(3-pyridinyl)acrylonitrile, which is purified by column chromatography over silica gel using CHCl3 as the eluent; yield 3.3 g (25.6%).

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