2-Vinylpyridine → 3-(2-Pyridinyl)Propanenitrile

Temperature

105 °C

3-(2-Pyridinyl)propionitrile is prepared in this example using the procedure of V. Boekelheide, et al., J. Am. Chem. Soc., 75, 3243 (1953). A solution of potassium cyanide (83.74 g) in water (160 ml) is added to a solution of freshly distilled 2-vinylpyridine (67.59 g) in acetic anhydrid (131.30 g) with the rate of addition adjusted to maintain gentle refluxing. When the addition is complete, the resulting dark red mixture is heated for about 17 hours at 105° C. in an oil bath with vigorous stirring. The cooled reaction mixture is adjusted to pH 8 with a saturated Na2CO3 solution. The mixture is extracted with CHCl3 (4×150 ml), washed with water, dried with Na2SO4, and evaporated to a dark viscous oil. The oil is fractionally distilled in vacuo through a Vigreaux column. After a small forerun containing 2-vinylpyridine (0.35 g), the desired 3-(2-pyridinyl)propionitrile is collected as a clear, fluorescent yellow-green, viscous oil: yield 59.8 g; 70.4%; bp 86° C. at 1.0 mm Hg.

1. temperatureto maintain gentle refluxing
2. additionWhen the addition
3. customThe cooled reaction mixture
4. extractionThe mixture is extracted with CHCl3 (4×150 ml)
5. washwashed with water
6. dry with materialdried with Na2SO4
7. customevaporated to a dark viscous oil
8. distillationThe oil is fractionally distilled in vacuo through a Vigreaux column
9. additionAfter a small forerun containing 2-vinylpyridine (0.35 g)
10. customthe desired 3-(2-pyridinyl)propionitrile is collected as a clear, fluorescent yellow-green, viscous oil

ORD record

ord-90fb82862d334e81b055c55346778174

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05008270