Water → 2-[(3-Cyano-4-phenyl-2-propylquinolin-6-yl)oxy]acetamide
Reaktionsgleichung
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH3:14])[C:6]([C:15]#[N:16])=[C:5]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl[CH2:24][C:25]([NH2:27])=[O:26].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:15]([C:6]1[C:7]([CH2:12][CH2:13][CH3:14])=[N:8][C:9]2[C:4]([C:5]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:3][C:2]([O:1][CH2:24][C:25]([NH2:27])=[O:26])=[CH:11][CH:10]=2)#[N:16]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A suspension of 6-hydroxy-4-phenyl-2-propylquinoline-3-carbonitrile (0.98 g, 3.4 mmol), chloroacetamide (0.36 g, 3.8 mmol) and potassium carbonate (0.55 g, 4.0 mmol) in N,N-dimethylformamide (10 ml) was stirred at 60° C. for 18 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give 2-[(3-cyano-4-phenyl-2-propylquinolin-6-yl)oxy]acetamide (1.0 g, yield 88%) as pale-yellow crystals.
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-503d01439946477d8ba8d4b6dcbd5257
- Quelldatensatz
- uspto-grants-2009_06
- Patentnummer
- US07547710B2
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