Dimethylcarbamoyl Chloride → 3-Chloropyridine-2-carbonitrile

A 2M solution of 3-chloropyridine 1-oxide (C125) (10 mL, 20 mmol) is combined with an additional 90 mL of CH2Cl2. Dimethylcarbamoyl chloride (2.03 mL, 22.0 mmol) is added drop-wise, followed by the addition of trimethyl silylcyanide (2.93 mL, 22.0 mmol) via syringe. The reaction stirred at rt for 10 days and is quenched with 10% K2CO3 (100 mL). The layers are allowed to separate, and the organic layer is dried over K2CO3, filtered, and concentrated to an orange solid. The crude material is chromatographed over 160 g slurry-packed silica eluting with 40% EtOAc/hexane. The fractions with the desired compound are collected and concentrated to yield 3-chloropyridine-2-carbonitrile (C126) as a white solid (59% yield). MS (EI) for C6H3ClN2, m/z: 138 (M)+.

1. customis quenched with 10% K2CO3 (100 mL)
2. customto separate
3. dry with materialthe organic layer is dried over K2CO3
4. filtrationfiltered
5. concentrationconcentrated to an orange solid
6. customThe crude material is chromatographed over 160 g slurry-packed silica eluting with 40% EtOAc/hexane
7. customThe fractions with the desired compound are collected
8. concentrationconcentrated

ORD record

ord-0160f3da25304753a2e02953f05222e4

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067515B2