p-Toluenesulfonic acid → HCID 11175796, compound

Participants

Reaction Steps

In argon atmosphere, a mixture of 3.70 g (18.50 mmol) of 1-(6-bromopyridin-2-yl)ethanone, 3.27 g (18.50 mmol) of 2,6-diisopropylaniline, 50 mg of TsOH, and 150 ml of toluene was refluxed for 2-3 h using a Soxhlet apparatus with an extraction thimble filled with anhydrous CaCl2. The reaction mixture was cooled to ambient temperature, passed through a short layer of silica gel 60 (40-63 um), and then evaporated to dryness. The crude product was recrystallized from 30 ml of methanol. Yield 3.63 g (56%) of yellow crystalline solid. Anal. calc. for C19H23BrN2: C, 63.51; H, 6.45, N, 7.80. Found: C, 63.44; H, 6.40, N, 7.93. 1H NMR (CDCl3): δ 8.31 (dd, J=7.7 Hz, J=0.6 Hz, 1H, 3-H in pyridine), 7.66 (t, J=7.7 Hz, 1H, 4-H in pyridine), 7.57 (dd, J=7.7 Hz, J=0.6 Hz, 1H, 5-H in pyridine), 7.14-7.16 (m, 2H, 3, 5-H in 2, 6-iPr2C6H3), 7.08 (m, 1H, 4-H in 2, 6-iPr2C6H3), 2.68 (sep, J=6.7 Hz, 2H, CHMe2), 2.17 (s, 3H, MeC═N), 1.13 (d, J=6.7 Hz, 6H, CHMe2), 1.12 (d, J=6.7 Hz, 6H, CHMe2).

Provenance & Evidence