Dimethylformamide → 5-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole
Reaktionsgleichung
[N+:1]([C:4]1[CH:5]=[C:6]([Cl:19])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:9]2)([O-:3])=[O:2].P(Cl)(Cl)(OCl)=O.CN([CH:29]=[O:30])C>ClCCl>[Cl:19][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:9]2[CH:29]=[O:30]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
7-Nitro-5-chloro-2-phenyl-1H-indole (1.0 g, 3.67 mmol) prepared in Preparation 26 was dissolved in dichloromethane (20 mL). Phosphoryloxychloride (0.84 g, 5.50 mmol) and DMF (0.80 g, 11.01 mmol) were added in drops thereto at 0° C., and the mixture was stirred for 6 h at room temperature. After completion of the reaction, the reaction was quenched by saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (0.5 g, Yield 45%).
Aufarbeitung
- customAfter completion of the reaction
- customthe reaction was quenched by saturated aqueous sodium hydrogen carbonate solution
- extractionThe reaction mixture was extracted with ethyl acetate
- washwashed with saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe solvent was removed under reduced pressure
- customthe residue was purified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-d21f37f80e3044ca96c055590a9f99ab
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US09000028B2
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