Reaktionsgleichung
[CH3:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([CH3:12])=[CH:5][C:3]=1[NH2:4].Cl.CO[CH2:16][CH2:17][C:18](OC)(OC)[CH3:19].[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].C(O)C>[N+:9]([C:7]1[C:6]([CH3:12])=[C:5]2[C:3](=[C:2]([CH3:1])[CH:8]=1)[N:4]=[CH:16][CH:17]=[C:18]2[CH3:19])([O-:11])=[O:10]Komponenten
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A mixture of 2,5-dimethyl-4-nitroaniline (0.96 g), ferric chloride hexahydrate (2.50 g), zinc chloride (0.094 g), concentrated hydrochloric acid (0.481 mL), and ethanol (8 mL) is heated to 60° C. 1,3,3-trimethoxybutane (0.73 mL) is added dropwise while the reaction mixture is kept at 60° C. The reaction mixture is heated at reflux overnight and cooled to room temperature. A solution of 10% aqueous sodium hydroxide is added, and the mixture is extracted three times with methylene chloride. The combined organic layers are dried over sodium sulfate, filtered and evaporated to afford a crude product. The crude product is purified by flash chromatography using 25% ethyl acetate in hexane as eluent, providing 6-nitro-4,5,8-trimethylquinoline.
Aufarbeitung
- customis kept at 60° C
- temperatureThe reaction mixture is heated
- temperatureat reflux overnight
- temperaturecooled to room temperature
- extractionthe mixture is extracted three times with methylene chloride
- dry with materialThe combined organic layers are dried over sodium sulfate
- filtrationfiltered
- customevaporated
- customto afford a crude product
- customThe crude product is purified by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-f54c31b105564ebf9ec27a26c5c28f03
- Quelldatensatz
- uspto-grants-1996_11
- Patentnummer
- US05578607
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