Sodium Hydroxide → 5-Chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Temperature

80 °C

A mixture of methyl-5-chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (0.36 g, 1.8 mmol) and 2.0 mL each MeOH and 1N NaOH was heated in a sealed vial to 80° C. for 1 h. The reaction was cooled to ambient temperature, and the methanol was removed by a stream of nitrogen. Water (2 ml) was added and the solution was adjusted to pH 1 with 6N HCl. A thick white precipitate formed which was partitioned between water and dichloromethane. The organic layer was removed and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were dried with Na2SO4, filtered, and concentrated to give an orange-yellow solid. The material was partitioned between 1N HCl and EtOAc. The organic layer was washed twice with 1N HCl, dried with Na2SO4, filtered, and concentrated to give the desired product as a light orange solid. MS (m/z): 188.0 (M+H)+. Calc'd for C7H6ClNO3: 187.58.

1. temperatureThe reaction was cooled to ambient temperature
2. customthe methanol was removed by a stream of nitrogen
3. additionWater (2 ml) was added
4. customA thick white precipitate formed which
5. customwas partitioned between water and dichloromethane
6. customThe organic layer was removed
7. extractionthe aqueous layer was extracted twice with dichloromethane
8. dry with materialThe combined organic layers were dried with Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give an orange-yellow solid
12. customThe material was partitioned between 1N HCl and EtOAc
13. washThe organic layer was washed twice with 1N HCl
14. dry with materialdried with Na2SO4
15. filtrationfiltered
16. concentrationconcentrated

ORD record

ord-5751e996e35d4659a4f6744d96506e01

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557996B2