Thionyl Chloride → HCID 86645104, compound

Participants

Reaction Steps

1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carboxylic acid (11.2 g, 50.6 mmol) was dissolved in thionyl chloride (70 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 (80 mL), and added dropwise to a mixed solution of 1,3-cyclohexanedione (4.98 g, 44.4 mmol), triethylamine (5.4 g, 53.3 mmol) and acetonitrile (20 mL), under ice cooling. After the stirring for a day at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. After separating the inorganic substance by filtration, the solvent was distilled off under reduced pressure, and thus obtained crystal was washed with diisopropylether, to obtain 14.5 g of a subject compound (yield: 90.5%).

Provenance & Evidence