Hydrochloric Acid → 3-Acetyl-2-chloropyridine

Temperature

130 °C

Water (1.3 mL) was added to a solution of diethyl 2-(2-chloronicotinoyl)malonate (31.7 mmol) in dimethylsulfoxide (50 mL). The pH of the reaction mixture was added adjusted to 5-6 by the addition of hydrochloric acid and the reaction mixture was heated at 130° C. for 2 h. The reaction mixture was then quenched with ice water (300 mL) and the aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried (sodium sulfate), and concentrated. The residue was purified by chromatography (1/20 ethyl acetate/petroleum ether to provide 1-(2-chloropyridin-3-yl)ethanone in 56% yield as light yellow oil.

1. additionThe pH of the reaction mixture was added
2. customThe reaction mixture was then quenched with ice water (300 mL)
3. extractionthe aqueous layer was extracted with ethyl acetate (3×50 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried (sodium sulfate)
6. concentrationconcentrated
7. customThe residue was purified by chromatography (1/20 ethyl acetate/petroleum ether

ORD record

ord-200b0151ede24be3af5ab6cc1cdae35d

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273891B2