Trifluoroacetic acid → 4-(4-bromophenyl)-5,7-dichloro-1,2,3,4-tetrahydroquinoline-2-carboxylic Acid

HRID 47394

Reaction equation

HRID 47394 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].[Br:17][C:18]1[CH:25]=[CH:24][C:21](C=C)=[CH:20][CH:19]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(#N)C.C(O)C>[Br:17][C:18]1[CH:25]=[CH:24][C:21]([CH:11]2[C:3]3[C:4](=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=3[Cl:1])[NH:5][CH:12]([C:13]([OH:15])=[O:14])[CH2:10]2)=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 122813,5-DichloroanilineHCID 14798Sodium HydroxideHCID 162634-BromostyreneHCID 35932772-Ketobutyrate

Product 1

HCID 102010254-(4-bromophenyl)-5,7-dichloro-1,2,3,4-tetrahydroquinoline-2-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 40 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 4-bromostyrene 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-638a400385b2400ca3182ab90c300c27
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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