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Acetonitrile → 6-Chloro-4-o-tolyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

HRID 47402
Notes
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Reaction equation

HRID 47402 reaction equation
[Cl:1][C:2]1[CH:3]=C(C=[C:7](Cl)[CH:8]=1)N.[CH2:10]([C:12](=O)[C:13]([O-:15])=[O:14])[CH3:11].C[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=C.F[C:27](F)(F)[C:28](O)=O.[C:33](#[N:35])[CH3:34]>>[CH2:27]([O:15][C:13]([CH:12]1[CH2:10][CH:11]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:18][C:19]=2[CH3:20])[C:7]2[C:33](=[CH:34][CH:3]=[C:2]([Cl:1])[CH:8]=2)[NH:35]1)=[O:14])[CH3:28]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 119042-MethylstyreneHCID 122813,5-DichloroanilineHCID 35932772-Ketobutyrate

Product 1

HCID 99672766-Chloro-4-o-tolyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

Procedure

Compound 48 was prepared by the basic process from 5.0 mmol 3,5-dichloroaniline, 5.5 mmol ethylglyoxalate solution (50% toluene), 15.0 mmol 2-methylstyrene and 5.0 mmol trifluoroacetic acid in 30.0 ml acetonitrile.

Sources & evidence

ORD record
ord-838b3983153841b69700a407cbc8ce65
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699877B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes