Water → 1-(6-Methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 2194539Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([C:19]([O:21]CC)=[O:20])[C:10]2=[O:24])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([C:19]([OH:21])=[O:20])[C:10]2=[O:24])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4.1 g (13 mmol) of ethyl (6-methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in 1,4-dioxane (60 mL), and 2.6 g (19 mmol) of potassium carbonate and 100 mL of water were added thereto at room temperature. The resulting mixture was stirred for 3 hours at 60° C. The solvent was distilled off under reduced pressure from the reaction mixture, and the residue was dissolved in water and washed with chloroform. Concentrated hydrochloric acid was added to the aqueous phase to make the aqueous phase acidic, and the mixture was extracted with chloroform. The organic phase was dried and concentrated. Thus, 1.45 g of the title compound was obtained as colorless crystals (yield: 39%).

Workup

customat room temperature
distillationThe solvent was distilled off under reduced pressure from the reaction mixture
dissolutionthe residue was dissolved in water
washwashed with chloroform
additionConcentrated hydrochloric acid was added to the aqueous phase
extractionthe mixture was extracted with chloroform
customThe organic phase was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-a6b0945fd71a46b283b32430e61ddbf4
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334236B2

Reaction notes

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