Water → Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
Reaction equation
Cl[C:2]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:3]=1[C:4]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[H-].[Na+].O>O1CCCC1>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[N:13]1[C:2]2[C:3](=[CH:22][C:23]([F:27])=[C:24]([F:26])[CH:25]=2)[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]1Participants
5
Procedure
The solution of 3.0 g of ethyl 2-(2-chloro-4,5-difluorobenzoyl)-3-(2,4-difluorophenylamino)acrylate in 30 ml of anhydrous tetrahydrofuran was cooled to 10° C. 0.3 g (1.02 eq.) of 60% sodium hydride was added to the reaction mixture, which was refluxed for 4.5 hours. The reaction mixture was cooled to 5˜10° C. 54.6 ml of water was added to the reaction mixture, which was then stirred for 30 minutes. The organic layer was filtered under a reduced pressure and washed with a mixed solution of n-hexane and ether (1/1). The resulting wet cake was dried under a reduced pressure at 40˜45° C. for 6 hours to give 2.26 g of ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (Yield: 82.8%).
Workup
- temperaturewas refluxed for 4.5 hours
- temperatureThe reaction mixture was cooled to 5˜10° C
- filtrationThe organic layer was filtered under a reduced pressure
- washwashed with a mixed solution of n-hexane and ether (1/1)
- customThe resulting wet cake was dried under a reduced pressure at 40˜45° C. for 6 hours
Sources & evidence
- ORD record
- ord-f082c765f10441e0af7cc11f26b5168f
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07220861B2
Reaction notes
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