Water → HCID 57815363, compound

HRID 1510725Notes

Reaction equation

HRID 1510725 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:19].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O.[OH-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH3:21][O:20][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 57815227HCID 57815227, compound

Product 1

HCID 57815363HCID 57815363, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.11 g of 1-(2,2-dimethoxyethyl)-7-(trifluoromethyl)-3,4-dihydro-1,5-naphthyridin-2(1H)-one in 2 mL of dioxane, 0.16 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone was added, and the mixture was heated under reflux while stirring for 3 hours. Thereto were added water and ethyl acetate, the mixture was adjusted to pH 12 with a 2.0 mol/L aqueous sodium hydroxide solution, and the organic layer was separated. The organic layer was washed with an aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 90 mg of 1-(2,2-dimethoxyethyl)-7-(trifluoromethyl)-1,5-naphthyridin-2(1H)-one as a brown solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. washThe organic layer was washed with an aqueous sodium hydroxide solution
  5. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a0ccbab40aec4d02bcffde26d7cd6f29
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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