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Dimethylformamide → Methyl 3-formyl-1H-indole-5-carboxylate

HRID 1015438
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1015438
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.C(=O)([O-])[O-].[K+].[K+]>O>[CH:8]([C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([C:20]([O:22][CH3:23])=[O:21])[CH:15]=2)[NH:11][CH:12]=1)=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 2737635methyl 1H-indole-5-carboxylate

Produkt 1

HCID 19606277Methyl 3-formyl-1H-indole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A 1.28 ml portion of phosphoryl chloride was added dropwise to 8 ml of N,N-dimethylformamide under ice-cooling, followed by stirring at room temperature for 15 minutes. An 8 ml portion of an N,N-dimethylformamide solution of 2.00 g of methyl 1H-indole-5-carboxylate was added dropwise to this solution under ice-cooling, followed by stirring at room temperature for 1.5 hours. Under ice-cooling, 50 ml of water was added thereto and potassium carbonate was further added until the pH became 12, and the resulting solid was collected by filtration, washed with water and then dried over heating under a reduced pressure to obtain 2.19 g of methyl 3-formyl-1H-indole-5-carboxylate as a pale light brown solid.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 1.5 hours
  4. temperatureUnder ice-cooling
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with water
  7. customdried
  8. temperatureover heating under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a132fc67bde94ce19325d24809f21901
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07985764B2

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