Water → 6,7-Difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl ester

HRID 249295Notes

Reaction equation

HRID 249295 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([C:15](=[O:25])[C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=1Cl)=[CH:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH3:2].[H-].[Na+].O>C(COC)OC>[CH2:1]([O:3][C:4]([C:5]1[C:15](=[O:25])[C:16]2[C:17](=[CH:18][C:19]([F:23])=[C:20]([F:22])[CH:21]=2)[N:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:6]=1)=[O:26])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178471928HCID 178471928, compound

Product 1

HCID 104728546,7-Difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-(2-Chloro-4,5-difluorobenzoyl)-3-(4-fluoroanilino)-2-propenoic acid ethyl ester (11.0 g, 28.7 mmol) was dissolved in dimethoxyethane (200 ml) and cooled to 0°. Sodium hydride (1.65 g of a 50% suspension in mineral oil, 34.5 mmol) was added portionwise, and the mixture was heated to reflux for 3 hours. The reaction mixture was then poured into water (2 l) and the title product was collected by filtration (8.96 g, 25.8 mmol, 90% yield).

Workup

  1. temperaturecooled to 0°
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationthe title product was collected by filtration (8.96 g, 25.8 mmol, 90% yield)

Sources & evidence

ORD record
ord-a24e88e588544f42a30f80e543e07e48
Source dataset
uspto-grants-1993_05
Patent number
US05214051

Reaction notes

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