Pyridine → HCID 67026915, compound

Participants

Reaction Steps

A solution of 6-diethylamino-4-methyl-pyridine-2-carbaldehyde (427 mg, 2.22 mmol) and hydroxylamine hydrochloride (232 mg, 3.33 mmol) in NMP (10 mL) is stirred at 80° C. for 3 h, then at 90° C. for 10 h under microwave irradiation. The solution is cooled to 0° C. before pyridine (1.10 g, 11.3 mmol) and trifluoromethane sulfonic anhydride (3.15 g, 11.2 mmol) is added. The mixture is warmed to rt and stirred for 18 h before it is diluted with DCM (100 mL) and washed with 10% aq. citric acid solution (50 mL) followed by sat. aq. Na2CO3 solution. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 7:3 to give 6-diethylamino-4-methyl-pyridine-2-carbonitrile (329 mg) as a pale yellow solid; LC-MS: tR=1.02 min, [M+1]+=190.02. 1H NMR (CDCl3): δ 1.19 (t, J=7.0 Hz, 6H), 2.28 (s, 3H), 3.52 (q, J=7.0 Hz, 4H), 6.44 (s, 1H), 6.74 (s, 1H).

Provenance & Evidence