Trifluoroacetic acid → 7,9-dichloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid ethyl ester

HRID 47361

Reaction equation

HRID 47361 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].[CH:17]1[CH2:21]C=C[CH:18]=1.F[C:23](F)(F)[C:24](O)=O>C(#N)C>[CH2:23]([O:15][C:13]([CH:12]1[CH:10]2[CH2:21][CH:17]=[CH:18][CH:11]2[C:3]2[C:2]([Cl:1])=[CH:8][C:7]([Cl:9])=[CH:6][C:4]=2[NH:5]1)=[O:14])[CH3:24]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7612CyclopentadieneHCID 122813,5-DichloroanilineHCID 35932772-Ketobutyrate

Product 1

HCID 98832257,9-dichloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 1 was prepared in a yield of 89% by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol cyclopentadiene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-c93fb06d75a54a20946d718092cdbc12
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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