Phosphorus oxychloride → 5-chloro-1-methyl-1H-indole-3-carbaldehyde

HRID 1372753

Reaktionsgleichung

Reaktionsgleichung von HRID 1372753
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH:11]=[CH:10]2.[C:17](=O)(O)[O-:18].[Na+]>CN(C=O)C>[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH:11]=[C:10]2[CH:17]=[O:18]

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 108558435-Chloro-1-methylindole

Produkt 1

HCID 167237965-chloro-1-methyl-1H-indole-3-carbaldehydeAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

While stirring DMF (70 ml) at 0° C., phosphoryl chloride (4.97 ml, 53.3 mmol) was added dropwise in portions. After completion of the dropwise addition, the reaction mixture was stirred further for 10 minutes at the same temperature. A solution of 5-chloro-1-methylindole (5.89 g, 35.6 mmol) in DMF (10 ml) was added. The resulting mixture was stirred for cyclohexanecarboxylic time at 60° C. for 6 hours. The reaction mixture was cooled to room temperature, and added to a saturated aqueous solution of sodium bicarbonate in portions, followed by extraction with chloroform. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions, 5-chloro-1-methylindole-3-carbaldehyde (5.51 g, 80%) was obtained as a colorless solid.

Aufarbeitung

  1. additionAfter completion of the dropwise addition
  2. stirringThe resulting mixture was stirred for cyclohexanecarboxylic time at 60° C. for 6 hours
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions

Quellen und Nachweise

ORD-Eintrag
ord-c8a87e0ed7094c87bd05304189033a27
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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