Dimethylformamide → 3,5-Bis(3-chlorophenyl)-1-methylpyridin-4(1H)-one

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Reaction Steps

The aminoformylating reagent was made by adding 30 g. of dimethylformamide dropwise to 20 g. of phosgene in 150 ml. of chloroform at 0° C. A 10 g. portion of 1,3-bis(3-chlorophenyl)-2-propanone in 50 ml. of chloroform was then added. The mixture was stirred for 3 hours, after which 50 ml. of 40% aqueous methylamine was added. Chloroform was then evaporated from the mixture, and 200 ml. of ethanol and 50 ml. of additional 40% aqueous methylamine were added. The mixture was then stirred under reflux overnight. In the morning, the product was extracted as described in the example above, and chromatographed on a silica gel column with ethyl acetate containing successively larger quantities of methanol. The product, 3,5-bis(3-chlorophenyl)-1-methyl-4(1H)-pyridone, 0.85 g., melted at 164°-167° C.

Provenance & Evidence