2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → 2-Amino-7-chloro-3,5-dicarboethoxy-4-(m-trifluoromethylphenyl)-6-oxo-2-heptene

HRID 1904577Notes

Reaction equation

HRID 1904577 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:9](C2C=CC=CC=2)[CH:10]([C:16](=[O:19])[CH2:17][Cl:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.[NH2:28]/[C:29](/[CH3:36])=[CH:30]\[C:31]([O:33][CH2:34][CH3:35])=[O:32]>CCO>[NH2:28][C:29](=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:27])[F:26])[CH:4]=1)[CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16](=[O:19])[CH2:17][Cl:18])[CH3:36]

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 20037480Ethyl 2-(m-trifluoromethylphenyl-phenylmethyl)-4-chloro-3-oxobutanoate

Product 1

HCID 867431312-Amino-7-chloro-3,5-dicarboethoxy-4-(m-trifluoromethylphenyl)-6-oxo-2-hepteneYield 66.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(m-trifluoromethylphenyl-phenylmethyl)-4-chloro-3-oxobutanoate (8 g) and ethyl 3-aminocrotonate (3.4 g) in EtOH (80 ml) is heated to reflux temperature for 10 minutes, then it is cooled at room temperature and after usual work-up the residue is purified by column-chromatography on silica-gel (300 g, eluent Et2O/isopropylether 50/50) to give 6 g of 2-amino-7-chloro-3,5-dicarboethoxy-4-(m-trifluoromethylphenyl)-6-oxo-2-heptene as an oil.

Workup

  1. temperatureto reflux temperature for 10 minutes
  2. customafter usual work-up the residue is purified by column-chromatography on silica-gel (300 g, eluent Et2O/isopropylether 50/50)

Sources & evidence

ORD record
ord-f4184322056e40b1ad58f18a5fb71230
Source dataset
uspto-grants-1989_06
Patent number
US04839348

Reaction notes

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