Dimethylformamide → 5-Methoxy-2-methyl-1H-indole-3-carbaldehyde

HRID 1451516

Reaktionsgleichung

Reaktionsgleichung von HRID 1451516
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:17])=[CH:11]2.CN([CH:21]=[O:22])C>>[CH:21]([C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([O:7][CH3:6])[CH:9]=2)[NH:13][C:12]=1[CH3:17])=[O:22]

Komponenten

4

Edukt 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 706425-Methoxy-2-methylindole

Produkt 1

HCID 31595805-Methoxy-2-methyl-1H-indole-3-carbaldehyde

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 60 mL of DMF at 0° C. was added 10.1 mL of phosphorous oxychloride dropwise. The resulting solution was stirred 10 min at 0° C., then was treated dropwise with a solution of 5-methoxy-2-methylindole (16.2 g, 100 mmol) in 25 mL of DMF. The orange solution was wanned to 40° C. for 45 min, then cooled and quenched with ice. The mixture was then poured into 300 mL of ice water and treated with 100 mL of 10N NaOH. The resulting slurry was heated to reflux for 4 h, then cooled and filtered. The solid was rinsed with water and air-dried to give 18.7 g of the title compound.

Aufarbeitung

  1. waitThe orange solution was wanned to 40° C. for 45 min
  2. temperaturecooled
  3. customquenched with ice
  4. additionThe mixture was then poured into 300 mL of ice water
  5. additiontreated with 100 mL of 10N NaOH
  6. temperatureThe resulting slurry was heated
  7. temperatureto reflux for 4 h
  8. temperaturecooled
  9. filtrationfiltered
  10. washThe solid was rinsed with water
  11. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-dbd1fd0585d44420bba87a97ac19865e
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604253

Verknüpfte Notizen

Wird geladen…