Trifluoroacetic acid → 5,7-Dichloro-4-naphthalene-2-yl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

HRID 47367

Reaction equation

HRID 47367 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:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)=C.F[C:30](F)(F)[C:31](O)=O>C(#N)C>[CH2:30]([O:15][C:13]([CH:12]1[CH2:10][CH:11]([C:24]2[CH:23]=[CH:22][C:21]3[C:26](=[CH:27][CH:28]=[CH:19][CH:20]=3)[CH:25]=2)[C:3]2[C:4](=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=2[Cl:1])[NH:5]1)=[O:14])[CH3:31]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 122813,5-DichloroanilineHCID 132302-VinylnaphthaleneHCID 35932772-Ketobutyrate

Product 1

HCID 101355945,7-Dichloro-4-naphthalene-2-yl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 11 was prepared in a yield of 84% by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 2-vinylnaphthalene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-bffe6a37296f496b8008a9b371b5644d
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Linked notes

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