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-d1f34ef873174ceb9f83b33430ec3f08

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106066B2