Ammonia → HCID 118598845, compound

Temperature

45 °C

In a round bottom flask charged with ethyl 5-bromo-3-fluoro-6-oxo-1H-pyridine-2-carboxylate (4, 0.8 g, 3.03 mmol) at 0° C. was added liquid ammonia (15 mL, 3.03 mmol) in ethanol (5 mL). The stirred reaction mixture was warmed to 45° C. for 2 h. After the ester was completely consumed liquid ammonia and ethanol was evaporated under reduced pressure. Methanol was added and the mixture was refluxed for 2 h and filtered while hot. The volume of the filtrate was reduced by ⅔ and to the remaining methanol was added diethyl ether until solid precipitated. The solid was filtered and dried under vacuum to afford 5-bromo-3-fluoro-6-oxo-1H-pyridine-2-carboxamide (5) as a light brown solid. Yield: 0.6 g, 85%; 1H NMR (400 MHz, DMSO-d6) δ 7.88-7.86 (m, 1H), 7.67 (s, 1H), 7.50 (s, 1H).

1. customThe stirred reaction mixture
2. customwas evaporated under reduced pressure
3. additionMethanol was added
4. temperaturethe mixture was refluxed for 2 h
5. filtrationfiltered while hot
6. additionwas added diethyl ether until solid
7. customprecipitated
8. filtrationThe solid was filtered
9. customdried under vacuum

ORD record

ord-c28c753d8a594c9a81d8b6a13a42dd2c

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382248B2