Methyl iodide → 1-methyl-1H-indole-5-carbaldehyde

HRID 1362045

Reaktionsgleichung

Reaktionsgleichung von HRID 1362045
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].CI.[C:16](OCC)(=O)C>CN(C=O)C>[CH3:16][N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 589040Indole-5-carboxaldehyde

Produkt 1

HCID 75375341-methyl-1H-indole-5-carbaldehydeAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of indole-5-carbaldehyde (1.0 g, 6.9 mmol) in DMF (15 mL) was added sodium hydride (303 mg of 60% dispersion in oil, 7.59 mmol) in 3 portions. The mixture was stirred for 30 mins. Methyl iodide (1.96 g, 13.8 mmol) was then added and the mixture was stirred overnight. Ethyl acetate (200 mL) was added and solution was washed with H2O (3×20 mL) and brine (25 mL) dried over MgSO4 and concentrated to afford N-methylindole-5-carboxaldehyde as an orange oil (1.0 g, 91%). 1H NMR (200 MHz, CDCl3) δ 10.05 (s, 1H), 8.09 (s, 1H), 7.90-7.80 (m, 1H), 7.35-7.15 (m, 2H), 6.85-6.80 (m, 1H), 3.95 (s, 3H).

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. washsolution was washed with H2O (3×20 mL) and brine (25 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1e58c4510edc411f9995ba647d2f4e31
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

Verknüpfte Notizen

Wird geladen…