Trifluoroacetic acid → 5,7-dichloro-4-phenyl-1,2,3,4-tetrahydroquinoline-2-carboxylic Acid

HRID 47370Notes

Reaction equation

HRID 47370 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].C=C[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.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:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:10][CH:12]([C:13]([OH:15])=[O:14])[NH:5]2

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7501StyreneHCID 122813,5-DichloroanilineHCID 14798Sodium HydroxideHCID 35932772-Ketobutyrate

Product 1

HCID 99231615,7-dichloro-4-phenyl-1,2,3,4-tetrahydroquinoline-2-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 15 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol styrene 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-d3e2222c3045443591698a2b7c600b99
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Reaction notes

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