Water → HCID 67412454, Verbindung

HRID 909378

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:20](=[O:22])[CH2:19][CH:18]([CH2:23][CH2:24][CH3:25])[CH2:17][C:16]=3[NH:15][C:14]([CH3:26])=[C:13]2[C:27]#[N:28])[CH:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1[OH:8].[Br:29][CH:30]=[CH:31][CH2:32][CH2:33]Br.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:20](=[O:22])[CH2:19][CH:18]([CH2:23][CH2:24][CH3:25])[CH2:17][C:16]=3[NH:15][C:14]([CH3:26])=[C:13]2[C:27]#[N:28])[CH:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1[O:8][CH2:33][CH:32]=[CH:31][CH2:30][Br:29]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 4-(3-bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (3.04 g), 1,4-dibromobutene (11.68 g) and potassium carbonate (1.887 g) in dioxane (100 ml) was stirred at 80° C. for 5 h. The mixture was poured into water and extracted with dichloromethane. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in acetonitrile, washed with petroleum ether and heptane to remove most of the excess of dibromobutene. The acetonitrile layer was concentrated in vacuo and the residue recrystallized from dichloromethane and heptane. Yield: 3.02 g. MS-ESI: [M+H]+=579.2

Aufarbeitung

extractionextracted with dichloromethane
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in acetonitrile
washwashed with petroleum ether and heptane
customto remove most of the excess of dibromobutene
concentrationThe acetonitrile layer was concentrated in vacuo
customthe residue recrystallized from dichloromethane and heptane

Quellen und Nachweise

ORD-Eintrag: ord-472e39a4e23e46c19639a19e3b86dc75
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08017782B2

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