Water → 2-(6-Chloropyridin-3-yl)acetonitrile

Temperature

50 °C

A solution of 5.2 g (32 mmol) of 2-chloro-5-chloromethylpyridine dissolved in 40 mL of ethanol was treated with 20 mL of water and 2.4 g (37 mmol) of potassium cyanide. The mixture was stirred and heated at 50° C. for 20 hours. The dark mixture was then partitioned between dichloromethane and water and the organic layer was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to yield 4.54 g (92%) of Preparatory Compound E, (6-chloro-3-pyridinyl)acetonitrile, as a dark brown liquid: 1H NMR (CDCl3) δ 8.38 (d, J=3.0 Hz, 1H), 7.71 (dd, J=3.0 and 7.6 Hz, 1H), 7.42 (d, J=7.6 Hz, 1H), 3.80 (s, 2H) ppm. GCMS: (EI) m/z 152 (M+).

1. customThe dark mixture was then partitioned between dichloromethane and water
2. washthe organic layer was washed with brine
3. dry with materialdried over sodium sulfate
4. customThe solvent was removed under reduced pressure

ORD record

ord-003b505f35a049cd8c00f09aeb83e024

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557132B2