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

HRID 2194509Notes

Reaction equation

HRID 2194509 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[C:4]([C:12]([O:14]CC)=[O:13])[C:3]1=[O:17].O.[OH-].[Li+].O.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=[O:13])[C:3]1=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 67009665Ethyl 1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 670095981-Methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acidYield 89.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.66 g (7.1 mmol) of ethyl 1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in 1,4-dioxane (50 mL), and 0.45 g (11 mmol) of lithium hydroxide monohydrate and 10 mL of water were added to the solution at room temperature. The resulting mixture was stirred for 1.5 hours at room temperature. The reaction mixture was poured into an aqueous solution of sodium hydrogen carbonate, and the mixture was washed with ethyl acetate. The aqueous phase was acidified with citric acid, and then the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried, and concentrated. The residue was washed with diisopropyl ether, and 1.30 g (yield: 89%) of the title compound was obtained as colorless crystals.

Workup

  1. washthe mixture was washed with ethyl acetate
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. customdried
  5. concentrationconcentrated
  6. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-e13a651a7eca4cb5b35f94d78656127c
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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