2-Aminothiophene → ethyl 2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)-3-(thiophen-2-ylamino)prop-2-enoate

HRID 232682

Reaction equation

HRID 232682 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].[NH2:24][C:25]1[S:26][CH:27]=[CH:28][CH:29]=1>>[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:24][C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

3

Reactant 2

HCID 973732-AminothiopheneHCID 54293321Ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)3-ethoxyacrylate

Product 1

HCID 178471950ethyl 2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)-3-(thiophen-2-ylamino)prop-2-enoate

Procedure

Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)3-ethoxyacrylate (5.0 g)and 2-aminothiophene (2.22 g), the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-(2-thienyl)aminoacrylate, which is then treated with 60% sodium hydride as in Reference Example 22 to give ethyl 1-(2-thienyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.05 g), as white powder (recrystallized from ethyl acetate - n-hexane), m.p. 198°-200° C.

Sources & evidence

ORD record
ord-64696ba11ba74363a9412e92ee5151b6
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Linked notes

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