Chloroacetyl chloride → 2-Chloro-N-pyridin-2-yl-acetamide

A solution of 2-amino-pyridine (1.0 g) in dry dichloromethane (10.6 mL) under nitrogen at 0° C. was treated with triethylamine (1.63 mL) followed by slow addition of chloroacetyl chloride (0.93 mL). The reaction mixture was allowed to warm up to room temperature. After 2 hours, the mixture was partitioned between dichloromethane and water. The phases were separated and the aqueous layer was extracted with dichloromethane (×2). The combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated to give the crude product which was purified by silica gel chromatography eluting with 0-30% ethyl acetate/cyclohexane to give the title compound (1.43 g) as a pink solid. Further purification was achieved by trituration with 40-60 petroleum ether to give 1.15 g of the desired product. Crystallisation of a 0.94 g portion of the material from refluxing acetonitrile (2.4 mL) gave the sub-titled compound as a pink solid (0.73 g).

1. customthe mixture was partitioned between dichloromethane and water
2. customThe phases were separated
3. extractionthe aqueous layer was extracted with dichloromethane (×2)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over magnesium sulphate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give the crude product which
9. customwas purified by silica gel chromatography
10. washeluting with 0-30% ethyl acetate/cyclohexane

ORD record

ord-448583372ad84d8f929db2d17f329a2e

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329729B2