Sodium Hydroxide → 1-(2-Methoxyethyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid

Temperature

80 °C

Methyl 1-(2-methoxyethyl)-2-oxo-pyridine-4-carboxylate (1.56 g, 7.39 mmol), dioxane (16 mL) and NaOH (20 mL of 1 M, 20 mmol) were combined and the mixture was heated at 80° C. for 50 min. The solvent was evaporated under reduced pressure and the residue was dissolved in water before it was washed with EtOAc (3×). The aqueous layer was acidified with 1N HCl and was washed with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure to yield 1-(2-methoxyethyl)-2-oxo-pyridine-4-carboxylic acid (1.0 g, 69%) as a white solid. ESI-MS m/z calc. 197.2, found 198.3 (M+1)+; Retention time: 0.29 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.59 (s, 1H), 7.72 (d, J=7.0 Hz, 1H), 6.84 (d, J=1.6 Hz, 1H), 6.53 (dd, J=7.0, 1.6 Hz, 1H), 4.08 (t, J=5.2 Hz, 2H), 3.58 (t, J=5.2 Hz, 2H), 3.23 (s, 3H).

1. customThe solvent was evaporated under reduced pressure
2. dissolutionthe residue was dissolved in water before it
3. washwas washed with EtOAc (3×)
4. washwas washed with EtOAc (3×)
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. customthe solvent was evaporated under reduced pressure

ORD record

ord-2422e977e7e94083bbccfafe73695112

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365588B2