Sodium Cyanide → 2-(2-Chloropyridin-3-yl)acetonitrile

Temperature

80 °C

In a 250 mL round bottom flask was dissolved 3-(bromomethyl)-2-chloropyridine (7.2 g, 35 mmol) in MeOH (70 mL). To the solution was added sodium cyanide (3.4 g, 70 mmol), then attached a reflux condenser, stirred the mixture at 80° C., while monitoring the reaction by LCMS. After about 1.5 h, the reaction was cooled to RT, concentrated, diluted with EtOAc, upon which a white solid crashed out. The solids were filtered and rinsed with EtOAc. The organic filtrate was concentrated to yield a crude reddish brown solid. The solid was dissolved in EtOAc, and purified by silica gel chromatography eluting with 40-70% EtOAc/Hexanes. The product fractions were concentrated to yield 2-(2-chloropyridin-3-yl)acetonitrile as an off-white solid. MS m/z=153 [M+1]+. Calc'd for C7H5ClN2: 152.58.

1. customthe reaction by LCMS
2. temperaturethe reaction was cooled to RT
3. concentrationconcentrated
4. additiondiluted with EtOAc, upon which a white solid
5. filtrationThe solids were filtered
6. washrinsed with EtOAc
7. concentrationThe organic filtrate was concentrated
8. customto yield a crude reddish brown solid
9. custompurified by silica gel chromatography
10. washeluting with 40-70% EtOAc/Hexanes
11. concentrationThe product fractions were concentrated

ORD record

ord-e1401ad25f0b47cebf82e13c9138ff8c

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242961B2