2,4-Difluoroaniline → HCID 178471929, compound

HRID 232680Notes

Reaction equation

HRID 232680 reaction equation
[CH3:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:3]=1[C:4]([C:6](=[CH:12]OCC)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[F:24][C:25]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:26]=1[NH2:27]>>[CH3:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:3]=1[C:4]([C:6](=[CH:12][NH:27][C:26]1[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:25]=1[F:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

3

Reactant 2

HCID 97092,4-DifluoroanilineHCID 54293321Ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)3-ethoxyacrylate

Product 1

HCID 178471929HCID 178471929, compound

Procedure

Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate (5.0 g) and 2,4-difluoroaniline (2.02 g), the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-(2,4-difluorophenyl)aminoacrylate, which is then treated with 60% sodium hydride as in Reference Example 22 to give ethyl 1-(2,4-difluorophenyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (4.6 g), as pale yellow prisms (recrystallized from dichloromethane - n-hexane), m.p. 156°-157.5° C.

Sources & evidence

ORD record
ord-26ae09618f904b718c7e3d3eee1d44c4
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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