Trifluoroacetic acid → 6-Chloro-4-(2-methoxyphenyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

HRID 47411Notes

Reaction equation

HRID 47411 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].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1C=C.F[C:27](F)(F)[C:28](O)=O>C(#N)C>[CH2:27]([O:14][C:12]([CH:11]1[CH2:9][CH:10]([C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[O:17][CH3:16])[C:7]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:8]=2)[NH:6]1)=[O:13])[CH3:28]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 78124-ChloroanilineHCID 611532-VinylanisoleHCID 35932772-Ketobutyrate

Product 1

HCID 101546356-Chloro-4-(2-methoxyphenyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 58 was prepared by the basic process from 5.0 mmol 4-chloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 2-methoxystyrene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-95dc4ec5787e4f8290c77d36222d598a
Source dataset
uspto-grants-2004_03
Patent number
US06699877B2

Reaction notes

Loading…