Hydrochloric Acid → 6-Methoxy-1-methyl-1H-indole-3-carbaldehyde

HRID 1976723

Reaktionsgleichung

Reaktionsgleichung von HRID 1976723
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:12]=[O:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:16]I.Cl>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH:12]=[O:13])=[CH:8][N:9]2[CH3:16])=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9072146-Methoxy-1H-indole-3-carboxaldehyde

Produkt 1

HCID 13820106-Methoxy-1-methyl-1H-indole-3-carbaldehydeAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-methoxy-1H-indole-3-carboxaldehyde (1.65, 9.4 mm) in DMF (10 mL) was cooled to 0° C., and treated with NaH(11.3 mm). After stirring at room temperature for 1 hour, the mixture was cooled to 0° C., treated with CH3I (0.7 mL, 11.3 mm), then allowed to warm to room temperature overnight. After pouring into H2O (200 mL), the mixture was acidified with HCl and extracted with EtOAc (100 mL×2). The combined organic fractions were dried over MgSO4, filtered and evaporated to afford 6-methoxy-1-methyl-1H-indole-3-carboxaldehyde (1.78 g, 99%).

Aufarbeitung

  1. temperaturethe mixture was cooled to 0° C.
  2. temperatureto warm to room temperature overnight
  3. extractionextracted with EtOAc (100 mL×2)
  4. dry with materialThe combined organic fractions were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c70c54f8e082415f908c58c41ed3a9c5
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06228877B1

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