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

HRID 2194539
Notes
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Reaction equation

HRID 2194539 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67010881Ethyl (6-methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 670096411-(6-Methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acidYield 37.5%

Reagents, catalysts & solvents 1

HCID 312751,4-Dioxane
Solvent

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

  1. customat room temperature
  2. distillationThe solvent was distilled off under reduced pressure from the reaction mixture
  3. dissolutionthe residue was dissolved in water
  4. washwashed with chloroform
  5. additionConcentrated hydrochloric acid was added to the aqueous phase
  6. extractionthe mixture was extracted with chloroform
  7. customThe organic phase was dried
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes