Water → 1-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanone

Participants

Reaction Steps

20 g of 2,6-diacetylpyridine (0.123 mol), 19.08 g of 2-chloro-4,6-dimethylaniline (0.123 mol) and 0.5 g of p-toluenesulfonic acid were heated under reflux on a water separator in 500 ml of heptane for 75 min. The insoluble solid was filtered off. The solvent was distilled off from the filtrate down to 150 ml, and the remaining filtrate was cooled to room temperature, while stirring. 25.3 g of a yellow solid precipitated out. This was filtered off and recrystallized from 60 ml of hot isopropanol. A total of 12.9 g (0.043 mol) of 1-{6-[1-(2-chloro-4,6-dimethylphenylimino)ethyl]-pyridin-2-yl}ethanone were obtained in a yield of 35%.

Provenance & Evidence