Trifluoroacetic acid → 5,7-Dichloro-4-p-tolyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

HRID 47373

Reaction equation

HRID 47373 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].[CH3:17][C:18]1[CH:25]=[CH:24][C:21](C=C)=[CH:20][CH:19]=1.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:21]2[CH:24]=[CH:25][C:18]([CH3:17])=[CH:19][CH:20]=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 121611-Ethenyl-4-methylbenzeneHCID 122813,5-DichloroanilineHCID 35932772-Ketobutyrate

Product 1

HCID 101556515,7-Dichloro-4-p-tolyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 19 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 4-methylstyrene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-eae19811fc42418b9253f1ef9e5154b1
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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