Cyclopropylamine → ethyl 3-(cyclopropylamino)-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)prop-2-enoate

HRID 2396952Notes

Reaction equation

HRID 2396952 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([C:10](=[CH:16]OCC)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[C:6]([F:20])[C:5]([F:21])=[C:4]([F:22])[C:3]=1[F:23].[CH:24]1([NH2:27])[CH2:26][CH2:25]1>C(O)C>[CH3:1][C:2]1[C:7]([C:8]([C:10](=[CH:16][NH:27][CH:24]2[CH2:26][CH2:25]2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[C:6]([F:20])[C:5]([F:21])=[C:4]([F:22])[C:3]=1[F:23]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 54293321Ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)3-ethoxyacrylate

Product 1

HCID 178471859ethyl 3-(cyclopropylamino)-2-(2,3,4,5-tetrafluoro-6-methylbenzoyl)prop-2-enoateYield 91.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(6-methyl-2,3,4,5-tetrafluorobenzoyl)-3-ethoxyacrylate (5 g) is dissolved in ethanol (25 ml) and thereto cyclopropylamine (1.0 g) is added dropwise under ice-cooling. After stirring at room temperature for 30 minutes, the mixture is concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane : n-hexane=1 : 1) to give ethyl 2-(6-methyl-2,3,4,5-tetrafluorobenzoyl)-3 -cyclopropylaminoacrylate (4.74 g), as white plates, m.p. 78°-79° C. (recrystallized from petroleum ether--n-hexane).

Workup

  1. temperaturecooling
  2. concentrationthe mixture is concentrated
  3. customthe residue is purified with column chromatography (silica-gel, dichloromethane : n-hexane=1 : 1)

Sources & evidence

ORD record
ord-1db02a65491d49fd9141619991997e50
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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