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Dimethylformamide → 2-Chloro-5-methoxy-1-phenyl-1h-indole-3-carbaldehyde

HRID 1510079
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1510079
CN(C=O)C.[CH2:6]([Cl:8])Cl.P(Cl)(Cl)(Cl)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:20](=[O:31])[CH2:19]2>C(Cl)(Cl)Cl.N1C=CC=CC=1.CC(=O)OCC>[Cl:8][C:6]1[N:21]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:22]2[C:18]([C:19]=1[CH:20]=[O:31])=[CH:17][C:16]([O:15][CH3:14])=[CH:24][CH:23]=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 136034182h-Indol-2-one,1,3-dihydro-5-methoxy-1-phenyl-

Produkt 1

HCID 872052842-Chloro-5-methoxy-1-phenyl-1h-indole-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049
Pyridine
Lösungsmittel
HCID 6212ChloroformLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of DMF (2.3 ml) and DCM (2.3 ml) under argon was cooled to 0° C. With stirring, phosphorus oxychloride (2.14 ml, 22.9 mmol) was added within 15 min, and the mixture was stirred for further 30 min at 0° C. Then the compound of step 2 (557 mg, 2.33 mmol), dissolved in chloroform (5.77 ml) and pyridine (1.15 ml), was added to the cooled solution. The reaction mixture was stirred at room temperature overnight. The mixture was slowly poured into 300 ml of ice and after a few minutes EA was added. The organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography of the residue on silica gel (EA/HEP 1:8) yielded 456 mg of the title compound as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred for further 30 min at 0° C
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. additionwas added
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83d74cc4b65541d9a060479d76a0a81f
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08211885B2

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