Dichloromethane → HCID 20548496, compound

Participants

Reaction Steps

A 1.1 g. portion of 3-acetyl-5-(3-chlorophenyl)-1-methyl-4(1H)-pyridinone was dissolved in 100 ml. of dichloromethane, and to it was added dropwise a solution of 1.06 g. of N-chlorosuccinimide in 50 ml. of dichloromethane. After the addition, the reaction mixture was stirred at reflux for 2 days, during which time two additional 0.5 g. portions of N-chlorosuccinimide were added. The mixture was then cooled, diluted with additional dichloromethane, and washed twice with 2 N sodium hydroxide solution. The organic portion was dried over magnesium sulfate, filtered and evaporated under vacuum. The residue was recrystallized from dichloromethane/hexane to obtain 0.4 g. of the desired product, m.p. 201°-202°. Nmr analysis in DMSOd6 showed peaks at δ8.50-8.55 (d, 1H, pyridine); 8.10-8.16 (d, 1H, pyridine); 7.3-8.8 (m, 5H, aromatic and CHCl2); 3.81 (s, 3H, N--CH3).

Provenance & Evidence