Dimethylformamide → 2-Acetyl-7-methoxy-3-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline
Reaktionsgleichung
[H-].[Na+].[CH3:3][CH:4]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][C:11]([O:17][CH3:18])=[CH:12][CH:13]=3)[C:8]=2[CH2:7][CH2:6][N:5]1[C:19](=[O:21])[CH3:20].CN(C=[O:26])C>>[C:19]([N:5]1[CH2:6][C:7]2[C:8](=[O:26])[C:9]3[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=3[NH:15][C:16]=2[CH:4]1[CH3:3])(=[O:21])[CH3:20]Komponenten
Versuchsvorschrift
NaH (1.2 eq; 60% suspension in oil) is added to a solution of 1-methyl-2-acetyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (1.56 g; 6.0 mmol) in DMF (20 ml). The mixture is stirred under an oxygen atmosphere for 48 hours, further NaH (1.1 eq) is then added and stirring is continued overnight. The DMF is then distilled off under reduced pressure. The crude product is taken up in water and then filtered. Saturated NH4Cl solution is added to the aqueous phase. The mixture is stirred for 30 minutes. The precipitate is filtered off and then washed successively with water, an MeOH/CH2Cl mixture (10/90), acetone and then ethyl acetate. After drying, 2-acetyl-7-methoxy-3-methyl-9-oxo-1,3,4,9-tetrahydropyrrolo[3,4-b]quinoline is obtained (yield=45%).
Aufarbeitung
- stirringstirring
- waitis continued overnight
- distillationThe DMF is then distilled off under reduced pressure
- filtrationfiltered
- additionSaturated NH4Cl solution is added to the aqueous phase
- stirringThe mixture is stirred for 30 minutes
- filtrationThe precipitate is filtered off
- washwashed successively with water
- customAfter drying
Quellen und Nachweise
- ORD-Eintrag
- ord-e68ba8361a354520bc0875d882399971
- Quelldatensatz
- uspto-grants-2002_01
- Patentnummer
- US06335346B1
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