3,5-Dichloro-2,4-difluorobenzoyl fluoride → ethyl 3-(cyclopropylamino)-2-(3,5-dichloro-2,4-difluorobenzoyl)prop-2-enoate

HRID 256312Notes

Reaction equation

HRID 256312 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[F:11])[C:5](F)=[O:6].[Cl:14][C:15]1[C:16]([F:35])=[C:17]([CH:30]=[C:31]([Cl:34])[C:32]=1[F:33])[C:18]([C:20](=COCC)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:19].ClC1C=C2C(=C(Cl)C=1F)[N:43]([CH:49]1[CH2:51][CH2:50]1)[CH:42]=[C:41]([C:52]([O:54][CH2:55][CH3:56])=[O:53])C2=O>>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][C:18](=[O:19])[C:17]1[CH:30]=[C:31]([Cl:34])[C:32]([F:33])=[C:15]([Cl:14])[C:16]=1[F:35])[CH3:25].[Cl:1][C:2]1[C:3]([F:13])=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[F:11])[C:5]([C:41](=[CH:42][NH:43][CH:49]1[CH2:50][CH2:51]1)[C:52]([O:54][CH2:55][CH3:56])=[O:53])=[O:6]

Participants

5

Reactant 3

HCID 54637643,5-Dichloro-2,4-difluorobenzoyl fluorideHCID 13579170Ethyl 6,8-dichloro-1-cyclopropyl-7-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateHCID 53830954Ethyl 2-(3,5-dichloro-2,4-difluoro-benzoyl)-3-ethoxy-acrylate

Product 2

HCID 13579168Ethyl(3,5-dichloro-2,4-difluoro-benzoyl)-acetateYield 43%HCID 178471860ethyl 3-(cyclopropylamino)-2-(3,5-dichloro-2,4-difluorobenzoyl)prop-2-enoateYield 96%

Procedure

3,5-Dichloro-2,4-difluoro-benzoyl fluoride is reacted analogously to Example A, the reaction passing through the following stages: ethyl(3,5-dichloro-2,4-difluoro-benzoyl)-acetate (yield: 43%, boiling point 133° C./2.5 mm Hg), ethyl 2-(3,5-dichloro-2,4-difluoro-benzoyl)-3-ethoxy-acrylate (crude yield: 91%, oil), ethyl 2-(3,5-dichloro-2,4-difluoro-benzoyl)-3-cyclopropylamino-acrylate (yield: 96%, melting point 71°-74° C.), ethyl 6,8-dichloro-1-cyclopropyl-7-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (yield: 97%, melting point 215°-217° C., with decomposition) and 6,8-dichloro-1-cyclopropyl-7-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (yield: 93%; melting point 204°-206° C.).

Sources & evidence

ORD record
ord-24c561b30ebb47619a5df7b67320ca2f
Source dataset
uspto-grants-1987_10
Patent number
US04703047

Reaction notes

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