p-Toluenesulfonic acid → 1-{6-[(1E)-N-(2,6-Dimethylphenyl)ethanimidoyl]pyridin-2-yl}ethan-1-one

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Reaction Steps

1-(6-Acetyl-pyridin-2-yl)-ethanone 2 (22.2 g, 0.0136 mole), 15.0 g (0.124 mol) of 2,6-dimethyl-phenylamine 3, 300 ml of n-propanol, and a few crystals of p-toluenesulfonic acid were stirred at room temperature for 36 h in 500 ml flask under a flow of nitrogen. The resultant yellow precipitate was filtered and washed by 20 ml of methanol. It was then dried at 1-mm vacuum overnight. The yield of 1-{6-[1-(2,6-dimethyl-phenylimino)-ethyl]-pyridin-2-yl}-ethanone 1 was 12.86 g (39%) as a yellow solid. 1H NMR (500 MHz, CD2Cl2, TMS): δ2.00 (s, 6H, Me), 2.20 (s, 3H, Me), 2.70 (s, 3H, Me), 6.90 (t, 3JHH=8.1 Hz, 1H, Arom-H), 7.10 (d, 3JHH=8.1 Hz, 2H, Arom-H), 7.95 (t, 3JHH=8.0 Hz, 1H, Pyr-H), 8.10 (d, 3JHH=8.0 Hz, 1H, Py-H), 8.55 (d, 3JHH=8.0 Hz, 1H, Py-H). 13C NMR (500 MHz, CD2Cl2, TMS (selected signals)): δ167.1 (C═N), 200.1 (C═O). Anal. Calculated for C17H18N2O (Mol. Wt.: 266.34): C, 76.66; H, 6.81; N, 10.52, Found: C, 76.69; H, 6.84; N, 10.57.

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