1-Fluoro-3-nitrobenzene → Ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylate

HRID 1067831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067831
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12].[H-].[Na+].F[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12]

Komponenten

5

Edukt 3

HCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 21194451HCID 21194451, Verbindung

Produkt 1

HCID 21194305Ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylateAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

After 0.50 g (1.97 mmol) of ethyl 4-chloro-7-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.16 g (3.94 mmol) of 60% sodium hydride and 10 ml of dimethylformamide, the suspension was stirred at room temperature for 30 minutes. Then 0.28 g (1.97 mmol) of 1-fluoro-3-nitrobenzene was added to the solution at room temperature followed by stirring for 3 hours at 150° C. After cooling, the reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was isolated and purified by silica gel column chromatography to give 0.18 g (24.3%) of ethyl 4-chloro-1-methyl-7-(3-nitrophenoxy)-2-indolecarboxylate.

Aufarbeitung

  1. stirringby stirring for 3 hours at 150° C
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured onto ice water
  4. extractionThe resulting mixture was then extracted three times with ethyl acetate
  5. washThe combined extracts were washed with saturated sodium chloride aqueous solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was isolated
  9. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2aab6ffc57ee4292a6b2b2de09700c4a
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248772B1

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