HCID 58707375, compound → 3-Acetyl-2-chloropyridine

Temperature

130 °C

A solution of diethyl 2-(2-chloronicotinoyl)malonate (267 mmol) in dimethylsulfoxide (100 ml) was added dropwise over 1.5 h to a 130° C. solution of water (10 mL) in dimethylsulfoxide (260 mL). The reaction mixture was maintained at 130° C. for an additional 2 h and was allowed to cool to rt. The reaction mixture was diluted with cold (0° C.) water (500 mL) and was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (5×200 mL), dried (sodium sulfate), and concentrated. The residue was purified by chromatography (10/1 petroleum ether/ethyl acetate) to provide 1-(2-chloropyridin-3-yl)ethanone 52% yield as yellow oil.

1. temperatureto cool to rt
2. extractionwas extracted with ethyl acetate (3×200 mL)
3. washThe combined organic layers were washed with brine (5×200 mL)
4. dry with materialdried (sodium sulfate)
5. concentrationconcentrated
6. customThe residue was purified by chromatography (10/1 petroleum ether/ethyl acetate)

ORD record

ord-5a4e1ef892e944fa84157507b92b625b

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273891B2