Acetic Acid → HCID 178470056, compound

HRID 1949154Notes

Reaction equation

HRID 1949154 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:24])[CH2:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:12]=1[C:21](=O)[CH3:22])=[O:9])[CH3:4].CC(O)=O>CCO.[Cl-].[Na+].O>[CH2:3]([O:5][C:6]([C:7]1[C:8]([OH:9])=[N:10][C:11]2[C:12]([C:21]=1[CH3:22])=[CH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)=[O:24])[CH3:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 67133787HCID 67133787, compound

Product 1

HCID 178470056HCID 178470056, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

235 mg (60% in mineral oil, 5.89 mmol) sodium hydride were added to a solution of 1.7 g (5.36 mmol) 3-(2-acetyl-5-(trifluoromethyl)phenylamino)-3-oxopropanoic acid ethyl ester in EtOH (16 ml) and the mixture was refluxed for 3 h and stirred for a further 16 h at RT. Then 1.34 ml (6.70 mmol) AcOH were added and the mixture was diluted with EE (30 ml) and brine (10 ml). The phases were separated and the organic phase was dried over MgSO4, filtered and concentrated to small volume under vacuum. Crystallisation (EE) of the residue yielded 920 mg (3.07 mmol, 57%) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum
  6. customCrystallisation (EE) of the residue

Sources & evidence

ORD record
ord-2aa2da391daa48deaa9a92aee26f90be
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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