Trifluoroacetic acid → 8-chloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid ethyl ester

HRID 47363

Reaction equation

HRID 47363 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]([C:11](=O)[C:12]([O-:14])=[O:13])[CH3:10].[CH:16]1[CH2:20]C=C[CH:17]=1.F[C:22](F)(F)[C:23](O)=O>C(#N)C>[CH2:22]([O:14][C:12]([CH:11]1[CH:9]2[CH2:20][CH:16]=[CH:17][CH:10]2[C:7]2[CH:8]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[NH:6]1)=[O:13])[CH3:23]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7612CyclopentadieneHCID 78124-ChloroanilineHCID 35932772-Ketobutyrate

Product 1

HCID 99654498-chloro-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinoline-4-carboxylic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 3 was prepared in a yield of 89% by the basic process from 5.0 mmol 4-chloroaniline, 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-0a43b64858bc4a909c3d85b6456cc7da
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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