5-Bromo-3-cyano-2-hydroxypyridine synthesis
- Product Name:5-Bromo-3-cyano-2-hydroxypyridine
- CAS Number:405224-22-8
- Molecular formula:C6H3BrN2O
- Molecular Weight:199
20577-27-9
405224-22-8
General procedure for the synthesis of 5-bromo-2-oxo-1,2-dihydropyridine-3-carbonitrile from 2-oxo-1,2-dihydropyridine-3-carbonitrile: 2-oxo-1,2-dihydropyridine-3-carbonitrile (50 mg, 0.42 mmol) and sodium acetate (69 mg, 0.84 mmol) were dissolved in 5 mL of glacial acetic acid at room temperature, and stirred until complete dissolution. Subsequently, bromine (21.5 μL, 0.42 mmol) was slowly added to the solution and the reaction lasted for 2 hours. Upon completion of the reaction, the mixture was concentrated under vacuum to remove the acetic acid. The crude product was purified by column chromatography (using ethyl acetate as eluent) to afford 5-bromo-2-oxo-1,2-dihydropyridine-3-carbonitrile (69 mg, 75% yield) as a yellow solid. Melting point: 216~217°C. 1H NMR (400MHz, CD3COCD3): δ11.70 (s, 1H), 8.22 (d, J = 2.8Hz, 1H), 8.05 (d, J = 2.8Hz, 1H).
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Yield:405224-22-8 88%
Reaction Conditions:
Stage #1: pyrid-2-one-3-carbonitrilewith acetic acid at 130;
Stage #2: with bromine for 3 h;
Steps:
1.2 Step 2: 5-bromo-2-oxo-1,2-dihydropyridine-3-carbonitrile
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 130°C. 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.
References:
KR101936851,2019,B1 Location in patent:Paragraph 0173; 0181-0184
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