Trifluoroacetic acid → 5,7-dichloro-3-methyl-4-(2,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic Acid Ethyl Ester

HRID 47401

Reaction equation

HRID 47401 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]/[CH:18]=[CH:19]\[C:20]1[CH:31]=[C:28]([O:29][CH3:30])[C:25]([O:26][CH3:27])=[CH:24][C:21]=1[O:22][CH3:23].F[C:33](F)(F)[C:34]([OH:36])=[O:35]>C(#N)C>[CH2:10]([O:36][C:34]([CH:33]1[CH:18]([CH3:17])[CH:19]([C:20]2[CH:31]=[C:28]([O:29][CH3:30])[C:25]([O:26][CH3:27])=[CH:24][C:21]=2[O:22][CH3:23])[C:3]2[C:4](=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=2[Cl:1])[NH:5]1)=[O:35])[CH3:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 122813,5-DichloroanilineHCID 35932772-KetobutyrateHCID 5281758Beta-Asarone

Product 1

HCID 101826315,7-dichloro-3-methyl-4-(2,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 47 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol β-asaron and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-b3314ddbf4d24b39acf27f68fdb1c33c
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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