Methyl iodide → 1-Methyl-5-nitro-1H-indole-3-carbaldehyde

HRID 618105

Reaktionsgleichung

Reaktionsgleichung von HRID 618105
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]=[O:14])([O-:3])=[O:2].[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:15][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([CH:13]=[O:14])=[CH:8]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2460395-nitro-1H-indole-3-carbaldehyde

Produkt 1

HCID 128715121-Methyl-5-nitro-1H-indole-3-carbaldehydeAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

5-Nitroindole-3-carboxaldehyde (2 g) was dissolved in N,N-dimethylformamide (40 ml), and potassium carbonate (4.0 g) and methyl iodide (5 ml) were added thereto, followed by stirring at 60° C. for 24 hours. The reaction solution was subjected to partitioning with chloroform, methanol and water, and the organic layer was dried over magnesium sulfate. After concentration under reduced pressure, the residue was rinsed with ethyl acetate to give 1-methyl-5-nitroindole-3-carboxaldehyde (Compound III-2, 1.99 g).

Aufarbeitung

  1. customto partitioning with chloroform, methanol and water
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationAfter concentration under reduced pressure
  4. washthe residue was rinsed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9b7c0d8c56f747a5a79040795b1e06b1
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952355

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