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

HRID 47371
Notes
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Reaction equation

HRID 47371 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][CH:23]=[CH:22][C:19]=1C=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:19]2[CH:22]=[CH:23][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])[CH3:28]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 119042-MethylstyreneHCID 122813,5-DichloroanilineHCID 35932772-Ketobutyrate

Product 1

HCID 101333515,7-Dichloro-4-o-tolyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

Compound 16 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 2-methylstyrene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-789bdd48cb9d4fae8eea910eb6e08d9b
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699877B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes