Trifluoroacetic acid → 5,7-Dichloro-4-(3-chlorophenyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

HRID 47388

Reaction equation

HRID 47388 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[CH2:10]([C:12](=O)[C:13]([O-:15])=[O:14])[CH3:11].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)C=C.F[C:27](F)(F)[C:28](O)=O>C(#N)C>[CH2:27]([O:15][C:13]([CH:12]1[CH2:10][CH:11]([C:24]2[CH:23]=[CH:20][CH:19]=[C:18]([Cl:17])[CH:25]=2)[C:3]2[C:4](=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=2[Cl:1])[NH:5]1)=[O:14])[CH3:28]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 122813,5-DichloroanilineHCID 14905m-ChlorostyreneHCID 35932772-Ketobutyrate

Product 1

HCID 102216605,7-Dichloro-4-(3-chlorophenyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 34 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 3-chlorostyrene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-af8bd26f9ff54f229d34806629b0c758
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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