2,6-Diacetylpyridine → 2,6-Bis[1-(2-chloro-4,6-dimethylphenylimino)ethyl]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-diacetylpyridine (35 g, 0.21 mol) in THF (1.21) was added 2-chloro-4,6-dimethylaniline (76.7 g, 2.3 eq) and Sicapent (45 g). The reaction mixture was refluxed overnight. Then additional 2-chloro-4,6-dimethylaniline (25 g, 0.7 eq) and Sicapent (25 g) were added and once again refluxed overnight. The suspension was cooled to 22° C., filtered and washed with two times THF (75 ml). The mother liquor was concentrated (90%) and methanol was added to precipitate the product, which was washed two times with methanol (50 ml) and dried under high vacuum. 68.8 g of a yellow powder was isolated (y=73.1%)

Provenance & Evidence