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

HRID 47377Notes

Reaction equation

HRID 47377 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:23]([CH3:26])=[CH:22][C:19]=1C=C.F[C:28](F)(F)[C:29](O)=O>C(#N)C>[CH2:28]([O:15][C:13]([CH:12]1[CH2:10][CH:11]([C:19]2[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:18]=2[CH3:17])[C:3]2[C:4](=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=2[Cl:1])[NH:5]1)=[O:14])[CH3:29]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 122813,5-DichloroanilineHCID 162652,5-DimethylstyreneHCID 35932772-Ketobutyrate

Product 1

HCID 102930235,7-Dichloro-4-(2,5-dimethylphenyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 23 was prepared in a yield of 89% by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 2,5-dimethylstyrene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-8226bf86d44e48a09d332d886061cc22
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Reaction notes

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