Pyridine → N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamide

Participants

Reaction Steps

15.7 g (41.7 mmol) of pyridinium dichromate were dissolved in 80 ml of methylene chloride, and 1.4 ml of trifluoroacetic acid and 0.9 ml of pyridine were added thereto. Next, 10 ml of a methylene chloride solution containing 10.0 g (27.8 mmol) of N-(3-isopropylphenyl)-N-(2-hydroxybutyl)-3-chlorophenylacetic amide obtained in Example 1 were added dropwise to the solution, while refluxed and stirred. Reaction was then carried out at the same temperature for 4 hours, and the resultant reaction mixture was then poured into 200 ml of diethyl ether. Insolubles were removed by filtration and the solvent was distilled off under reduced pressure, and the solution was then purified through silica gel column chromatography (an eluent: hexane/ethyl acetate=7/3) to obtain 7.61 g of the desired product in an oily state (yield: 76.2%).

Provenance & Evidence