Dimethylformamide → 2-Methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole-11-carbaldehyde
Reaktionsgleichung
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:15]3[CH2:16][C:17]4[C:22]([C:14]3=[CH:13][C:12]=2[N:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=4.CN(C)[CH:26]=[O:27]>>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:15]3[CH2:16][C:17]4[C:22]([C:14]3=[C:13]([CH:26]=[O:27])[C:12]=2[N:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=4Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Under argon and in an anhydrous medium, 291 μl (3.17 mmol) of phosphorus oxychloride are added dropwise to 6 ml of N,N-dimethylformamide maintained at 0° C.: after 15 minutes' stirring, 500 mg (2.11 mmol) of the compound obtained in Step D dissolved in 10 ml of N,N-dimethylformamide are added by transfer. The reaction mixture is stirred for 30 minutes at 0° C. and then for 2 hours at room temperature. The reaction mixture is evaporated to dryness and then taken up in water: the aqueous phase is rendered alkaline with a 6N sodium hydroxide solution and extracted several times with ethyl acetate. The combined organic phases are dried over magnesium sulphate, filtered and evaporated. After washing with a petroleum ether/diethyl ether mixture, the title compound is obtained in the form of a brown solid.
Aufarbeitung
- additionare added by transfer
- stirringThe reaction mixture is stirred for 30 minutes at 0° C.
- waitfor 2 hours at room temperature
- customThe reaction mixture is evaporated to dryness
- extractionextracted several times with ethyl acetate
- dry with materialThe combined organic phases are dried over magnesium sulphate
- filtrationfiltered
- customevaporated
- washAfter washing with a petroleum ether/diethyl ether mixture
Quellen und Nachweise
- ORD-Eintrag
- ord-57034cc585f44e9bb3f7030cf66f460a
- Quelldatensatz
- uspto-grants-2007_06
- Patentnummer
- US07235550B2
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