2-Acetylpyridine → 2,3,5,6-tetramethyl-N-(1-pyridin-2-ylethylidene)-benzene-1,4-diamine

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To a mixture of 2-acetylpyridine (0.30 ml, 0.26 mmol) and 2,3,5,6-tetramethyl-benzene-1,4-diamine (0.60 g, 0.37 mmol, 1.4 eq.) in toluene (2 ml) was added 2 drops of formic acid. The suspension was heated for three days at 50° C. The dark reddish suspension was cooled, filtered and the residue washed with cold toluene. The filtrate was evaporated, dissolved in chloroform (2 ml) and cooled to −78° C. for 0.5 hours before being filtered. Hexane was added to the filtrate and all volatiles were removed under reduced pressure to give 2,3,5,6-tetramethyl-N-(1-pyridin-2-ylethylidene)-benzene-1,4-diamine as a brown solid (0.31 g, 45%).

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