Sodium Hydroxide → 1-(2-Methoxyphenyl)-4-chloro-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH3:23])[C:15]=3[NH:14][C:13](=O)[C:12]=2[CH2:11][CH2:10]1.[OH-].[Na+].P(Cl)(Cl)([Cl:29])=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH3:23])[C:15]=3[N:14]=[C:13]([Cl:29])[C:12]=2[CH2:11][CH2:10]1Komponenten
Versuchsvorschrift
1-(2-Methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline (9.55 g) was dissolved in phosphoryl chloride (100 ml) and heated at reflux for 2.5 hours. After cooling, the solution was poured onto ice, made alkaline with aqueous sodium hydroxide solution, and extracted with dichloromethane. The organic extract was dried and evaporated, and the crude product purified by chromatography (silica gel, 50-100% diethyl ether in petroleum ether). The first compound to elute was 4-chloro-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline, m.p. 99°-101°. Later fractions containing the desired product were recrystallised from ethyl acetate, then ethyl acetate/ethanol to give1-(2-methoxyphenyl)-4-chloro-6-methoxy-2,3-dihydropyrrolo[3,2-c]quinoline, m.p. 183°-184°.
Aufarbeitung
- temperatureheated
- temperatureat reflux for 2.5 hours
- temperatureAfter cooling
- additionthe solution was poured onto ice
- extractionextracted with dichloromethane
- extractionThe organic extract
- customwas dried
- customevaporated
- customthe crude product purified by chromatography (silica gel, 50-100% diethyl ether in petroleum ether)
- washThe first compound to elute
- additionLater fractions containing the desired product
- customwere recrystallised from ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-d90e245ec69c4604a680eee94b281720
- Quelldatensatz
- uspto-grants-1991_09
- Patentnummer
- US05051508
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