Thionyl Chloride → HCID 86645104, compound

1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carboxylic acid (1.0 g, 4.5 mmol) was dissolved in thionyl chloride (5 mL), and the mixture was refluxed for 2 hours. The reaction solution was concentrated under reduced pressure to obtain 1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carbonyl chloride. The obtained acid chloride was dissolved in acetonitrile (20 mL), and added dropwise to a mixed solution of 3-cyclopropyl-3-oxopropanenitrile (0.49 g, 4.5 mmol), triethylamine (0.55 g, 5.4 mmol) and acetonitrile (10 mL), under ice cooling. After the stirring for a day at room temperature, acetonecyanhydrin (0.04 g, 0.47 mmol) and triethylamine (0.55 g, 5.4 mmol) were further added thereto, and the mixture was stirred for a day at room temperature. The reaction mixture was concentrated under reduced pressure, and thus obtained residue was added with a mixture of aqueous saturated sodium bicarbonate and ethyl acetate for liquid separation. The obtained aqueous layer was added with diluted hydrochloric acid to give a pH of 3 to 4, and extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and thus obtained crystal was washed with ether, to obtain 0.29 g of a subject compound (yield: 20%).

1. temperaturethe mixture was refluxed for 2 hours
2. concentrationThe reaction solution was concentrated under reduced pressure

ORD record

ord-6f9fe244c1c14e7e96d19d2b3a0cb1cd

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076487B2