Trifluoroacetic acid → 5,7-Dichloro-4-m-tolyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

HRID 47372Notes

Reaction equation

HRID 47372 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:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)C=C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(#N)C.C(O)C>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:4]2[C:3]=1[CH:11]([C:24]1[CH:25]=[C:18]([CH3:17])[CH:19]=[CH:20][CH:23]=1)[CH2:10][CH:12]([C:13]([OH:15])=[O:14])[NH:5]2

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 75291-Ethenyl-3-methylbenzeneHCID 122813,5-DichloroanilineHCID 14798Sodium HydroxideHCID 35932772-Ketobutyrate

Product 1

HCID 99675545,7-Dichloro-4-m-tolyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 18 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 3-methylstyrene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile. Subsequent saponification was carried out using 1.0 ml of sodium hydroxide solution (6N water) in 20.0 ml of ethanol.

Sources & evidence

ORD record
ord-42723208356b4a9f8b42376100211d32
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Reaction notes

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