Water → HCID 67009484, compound

HRID 2194544Notes

Reaction equation

HRID 2194544 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[N:10]=2)[CH:5]=[C:4]([C:16]([O:18]CC)=[O:17])[C:3]1=[O:21].O.[OH-].[Li+].O.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:13])[F:14])[N:10]=2)[CH:5]=[C:4]([C:16]([OH:18])=[O:17])[C:3]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 67009647HCID 67009647, compound

Product 1

HCID 67009484HCID 67009484, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.24 g (4.1 mmol) of ethyl 1-methyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in 1,4-dioxane (50 mL), and 0.35 g (8.3 mmol) of lithium hydroxide monohydrate and 10 mL of water were added thereto at room temperature. The resulting mixture was stirred overnight 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 the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried, and concentrated. The residue was washed with normal-hexane, and thus 1.02 g of the title compound was obtained as colorless crystals (yield: 91%).

Workup

  1. customat room temperature
  2. washthe mixture was washed with ethyl acetate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated
  7. washThe residue was washed with normal-hexane

Sources & evidence

ORD record
ord-090e96e839d441acb05c7a297035cf9e
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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