Water → 1-Benzyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 2194518Notes

Reaction equation

[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[CH:11]=[C:10]([C:18]([O:20]CC)=[O:19])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[CH:11]=[C:10]([C:18]([OH:20])=[O:19])[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1.95 g (6.3 mmol) of ethyl 1-benzyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in 1,4-dioxane (30 mL), and 1.31 g (9.5 mmol) of potassium carbonate and 60 mL of water were added to this solution at room temperature. The resulting mixture was stirred for 3 hours at 50° C. The solvent of the reaction mixture was distilled off under reduced pressure, and the residue was dissolved in water. Concentrated hydrochloric acid was added to make the solution acidic, and the mixture was extracted with chloroform. The organic phase was dried, filtered, and concentrated, and thus 1.71 g (yield: 97%) of the title compound was obtained as colorless crystals.

Workup

distillationThe solvent of the reaction mixture was distilled off under reduced pressure
dissolutionthe residue was dissolved in water
additionConcentrated hydrochloric acid was added
extractionthe mixture was extracted with chloroform
customThe organic phase was dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-3a78a15bb8e94ae5b574259b0ad4ee14
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334236B2

Reaction notes

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