Water → 1-(2-Chloropyridin-4-yl)ethan-1-one

Temperature

-70 °C

In 440 ml of THF was suspended 22 g of 2-chloroisonicotinic acid, and under nitrogen flow, the mixture was cooled to −70° C. or lower, 245 ml of methyl lithium (1.14 M solution in diethyl ether) was added dropwise to the mixture. After stirring at the same temperature for an hour, a temperature of the mixture was raised to 0° C. over an hour, and stirred at the same temperature for further an hour. To the reaction mixture was added 500 ml of water, and the reaction mixture was extracted with ethyl acetate, washed with brine and dried over magnesium sulfate. Activated charcoal was added to the mixture, and after filtration, the filtrate was concentrated under reduced pressure to give 19.5 g of 4-acetyl-2-chloropyridine as colorless crystals. Melting point: 36° C.

1. temperaturea temperature of the mixture was raised to 0° C. over an hour
2. stirringstirred at the same temperature for further an hour
3. extractionthe reaction mixture was extracted with ethyl acetate
4. washwashed with brine
5. dry with materialdried over magnesium sulfate
6. additionActivated charcoal was added to the mixture
7. filtrationafter filtration
8. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-cd41311aa1d7417583ac8fc5c21bf528

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473695B2