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Acetic acid (34 ml) was added to 2-oxo-1,2-dihydropyridine-3-carbonitrile (6.28 g, 0.052 mol) and the mixture was heated to 130C. When the solid was dissolved, bromine (12.5 g, 0.078 mol) was added slowly and stirred at the same temperature for 3 hours.After the reaction solution was cooled to room temperature, dichloromethane and water were added. The organic layer was separated and the aqueous layer was washed with dichloromethane. The organic layer was collected, washed with brine, dried over anhydrous sodium sulfate and concentrated to give the desired compound (9.11 g, 88% yield) as a yellow solid.
75%
With bromine; sodium acetate; In acetic acid; at 20.0℃; for 2.0h;
5-Bromo-2-oxo-1,2-dihydropyridine-3-carbonitrile(12) To a stirring solutionof compound 11 (50 mg, 0.42 mmol)and NaOAc (69 mg, 0.84 mmol) in 5 mL glacial AcOH at room temperature was addedBr2 (21.5 muL, 0.42 mmol) for 2 h. The mixture was concentrated invacuum to remove AcOH. Purification by chromatography (EA) provided compound 12 (69 mg, 75%) as a yellow solid. MP:216~217C. 1H NMR (400 MHz, CD3COCD3): delta 11.70 (s, 1H), 8.22 (d, J= 2.8 Hz, 1H), 8.05 (d, J = 2.8 Hz, 1H).5
With bromine; In acetic acid; at 20.0℃; for 14.0h;
5-Bromo-2-oxo-1,2-dihydro-pyridine-3-carbonitrile Brornine (29 ml, 560 mmol) was added to a stirred solution of 2-oxo-1,2-dihydro-pyridine-3-carbonitrile (34 g, 280 mmol) in acetic acid (180 ml) at room temperature. After 14 hours the reaction mixture was concentrated in vacuo and the resulting oil was trituated with ethanol to afford the title compound as a solid. 1H NMR delta (d6 DMSO) 12.8 (brs, 1H), 8.4 (d, 1H), 8.1 (d, 1H).
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