[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[CH3:10][C:11]1[C:16]([CH3:17])=[C:15]([NH2:18])[C:14]([CH3:19])=[C:13]([CH3:20])[C:12]=1[NH2:21]>C1(C)C=CC=CC=1.C(O)=O>[CH3:17][C:16]1[C:11]([CH3:10])=[C:12]([NH2:21])[C:13]([CH3:20])=[C:14]([CH3:19])[C:15]=1[N:18]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2]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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