p-Toluenesulfonic acid → HCID 117652630, compound

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Reaction Steps

In argon atmosphere, a mixture of 3.70 g (18.50 mmol) of 1-(6-bromopyridin-2-yl)ethanone, 2.49 g (18.50 mmol) of 2,4,6-trimethylaniline, 50 mg of TsOH, and 150 ml of toluene was refluxed for 2.5 h using a Soxhlet apparatus with an extraction thimble filled with anhydrous CaCl2. The resulting mixture was cooled to ambient temperature, passed through a short layer of silica gel 60 (40-63 um), and then evaporated to dryness. Yield 5.59 g (95%) of dark-red solid. Anal. calc. for C16H17BrN2: C, 60.58; H, 5.40; N, 8.83. Found: C, 60.70; H, 5.56; N, 8.77. 1H NMR (CDCl3): δ 7.98 (dd, J=7.1 Hz, J=1.4 Hz, 1H, 3-H in pyridine), 7.63-7.71 (m, 2H, 4, 5-H in pyridine), 6.76 (s, 2H, 3, 5-H in mesityl), 2.70 (s, 3H, MeC═N), 2.20 (s, 3H, 4-Me in mesityl), 2.15 (s, 6H, 2, 6-Me in mesityl).

Provenance & Evidence