Dimethylformamide → Methyl 3-formyl-1H-indole-7-carboxylate

HRID 1825747

Reaktionsgleichung

Reaktionsgleichung von HRID 1825747
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].P(Cl)(Cl)(Cl)=O.CN(C=O)C.[CH3:21][O:22][C:23]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:33]=1[NH:32][CH:31]=[CH:30]2)=[O:24]>ClCCCl>[CH3:21][O:22][C:23]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:33]=1[NH:32][CH:31]=[C:30]2[CH:8]=[O:9])=[O:24]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 676694Methyl indole-7-carboxylateHCID 13765457DMF Phosphorus oxychloride

Produkt 1

HCID 762965Methyl 3-formyl-1H-indole-7-carboxylateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel3×

Versuchsvorschrift

To a stirred mixture of phosphorus oxychloride-dimethylformamide in anhydrous 1,2-dichloroethane (prepared by the slow addition of phosphorus oxychloride (0.43 ml, 4.6 mmol) to anhydrous DMF (0.35 ml, 4.6 mmol) in anhydrous 1,2-dichloroethane (6 ml) cooled below 5° C.) a solution of 7-methoxycarbonylindole (0.69 g, 4 mmol) in anhydrous 1,2-dichloroethane (6 ml) was dropwise below 5° C. The mixture was stirred at room temperature for 2 h and then was heated at 50° C. for 30 minutes. After cooling, the precipitate was filtered off and washed with 1,2-dichloroethane. This precipitate was suspended in aq Na2CO3 10% (30 ml) and stirred at room temperature for 20 minutes; dichloromethane was added and stirring was continued 10 minutes more. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and evaporated to yield 0.75 g (93%) of the entitled product. Mp: 153–4° C.

Aufarbeitung

  1. customwas dropwise below 5° C
  2. temperaturewas heated at 50° C. for 30 minutes
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. washwashed with 1,2-dichloroethane
  6. stirringstirred at room temperature for 20 minutes
  7. additiondichloromethane was added
  8. stirringstirring
  9. waitwas continued 10 minutes
  10. customThe organic phase was separated
  11. extractionthe aqueous phase was extracted with dichloromethane
  12. washThe combined organic extracts were washed with brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1b6c9aa600274133865828d9e9ab2640
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049312B1

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