Ethylamine → ethyl 3-(ethylamino)-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)prop-2-enoate

HRID 2396973Notes

Reaction equation

HRID 2396973 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].[CH2:24]([NH2:26])[CH3:25]>>[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:26][CH2:24][CH3:25])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 54293321Ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)3-ethoxyacrylate

Product 1

HCID 178464350ethyl 3-(ethylamino)-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)prop-2-enoate

Procedure

Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate (10.0 g) and ethylamine gas, the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethylaminoacrylate (9.0 g, white crystals), which is then treated with 60% sodium hydride (1.30 g) as in REFERENCE EXAMPLE 22 to give ethyl 1-ethyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (6.76 g), as pale yellow needles (recrystallized from dichloromethane--n-hexane), m.p. 197°-198° C.

Sources & evidence

ORD record
ord-67ee67cf23a14477942a5764239acc5a
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

Loading…