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

HRID 47400

Reaction equation

HRID 47400 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(=O)C([O-])=O)[CH3:11].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][CH3:27])=[CH:21][C:20]=1[O:28][CH3:29].F[C:31](F)(F)[C:32]([OH:34])=[O:33]>C(#N)C>[CH2:10]([O:34][C:32]([CH:31]1[CH:26]([CH3:27])[CH:25]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[C:20]([O:28][CH3:29])[CH:21]=2)[C:3]2[C:4](=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=2[Cl:1])[NH:5]1)=[O:33])[CH3:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7128Methyl isoeugenolHCID 122813,5-DichloroanilineHCID 35932772-Ketobutyrate

Product 1

HCID 101806825,7-Dichloro-4-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 46 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 1,2-dimethoxy-4-prop-1-enylbenzene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-41d411c9f7f148f097b128270da8a730
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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