Dimethylformamide → 5-methoxy-1-methyl-1H-indole-3-carbaldehyde

HRID 1089544

Reaktionsgleichung

Reaktionsgleichung von HRID 1089544
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[CH:11]2.[OH-].[Na+].CN(C)[CH:22]=[O:23]>>[CH:22]([C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([O:7][CH3:6])[CH:9]=2)[N:13]([CH3:17])[CH:12]=1)=[O:23]

Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 8198645-methoxy-1-methyl-1H-indole

Produkt 1

HCID 9259735-methoxy-1-methyl-1H-indole-3-carbaldehyde

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

While cooling in order to maintain the temperature of the reaction medium below 15° C., phosphorus oxychloride (9 ml) is added dropwise to 35 ml of dimethylformamide (DMF), and 5-methoxy-1-methylindole (14.1 g), dissolved in DMF (25 ml) is added in a single portion. The resulting heterogeneous mixture is heated to 110° C. for 1 minute, and then maintained at 65° C. for 30 minutes while being stirred mechanically. After the mixture has been allowed to cool, it is decomposed by adding 200 ml of ice-cold water, and then treated with 5N sodium hydroxide solution (100 ml). The precipitate formed is filtered off and recrystallized in ethanol, to give 14.53 g (87.7%) of colorless scales, m.p.=134° C.

Aufarbeitung

  1. temperatureWhile cooling in order
  2. additionis added in a single portion
  3. temperaturemaintained at 65° C. for 30 minutes
  4. temperatureto cool
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. customrecrystallized in ethanol
  8. customto give 14.53 g (87.7%) of colorless scales, m.p.=134° C.

Quellen und Nachweise

ORD-Eintrag
ord-fcd1736e14204c9a9eeb41b043e7158c
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04966971

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