Reaktionsgleichung
[N:1]1([C:7]2[CH:8]=[C:9]([C:14]([N+:19]([O-:21])=[O:20])=[C:15]([CH3:18])[C:16]=2[F:17])[NH:10][CH:11]2[CH2:13][CH2:12]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(O[CH:25]=[C:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])C>>[CH2:30]([O:29][C:27](=[O:28])[C:26](=[CH:25][N:10]([CH:11]1[CH2:12][CH2:13]1)[C:9]1[C:14]([N+:19]([O-:21])=[O:20])=[C:15]([CH3:18])[C:16]([F:17])=[C:7]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:8]=1)[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:31]Komponenten
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
To 3-(1-piperazinyl)-4-fluoro-5-methyl-6-nitro-N-cyclopropylaniline (1.57 g) is added diethyl ethoxymethylenemalonate (1.45 ml) and the mixture is heated at 150° C. for 25 hours. After cooling, the reaction product is purified by silica-gel column-chromatography (dichloromethane:methanol=100:1) to give diethyl[N-cyclopropyl-N-[3-(1-piperazinyl)-4-fluoro-5-methyl-6-nitrophenyl]aminomethylene]malonate (1.50 g). The product is dissolved in acetic anhydride (7.9 ml) and thereto conc. sulfuric acid (3.16 ml) is added dropwise at 50°-60° C., followed by stirring for 30 minutes. The resultant mixture is poured into ice-water, neutralized, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure. Purification by silica-gel column-chromatography (dichloromethane:methanol=10:1) to give ethyl 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (26 mg).
Aufarbeitung
- temperatureAfter cooling
- customthe reaction product is purified by silica-gel column-chromatography (dichloromethane:methanol=100:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-9e51f3bff8b34c81acfcb6e892f0cb4c
- Quelldatensatz
- uspto-grants-1996_10
- Patentnummer
- US05563138
Verknüpfte Notizen
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