Reaktion #481117

Reaktionsgleichung

Diethyl ethoxymethylmalonate

m-toluidine

→

ethyl 4-hydroxy-7-methyl-3-quinolinecarboxylate

Ausbeute 76.3%

Lösungsmittel

Dowtherm A

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to ambient temperature
2. 2
   Temperaturthe reaction mixture was heated
3. 3
   Temperaturat reflux for about 30 minutes
4. 4
   Temperaturto cool to ambient temperature
5. 5
   SonstigeThe resulting precipitate was isolated by filtration
6. 6
   Waschenrinsed with acetone
7. 7
   Sonstigedried

Vorschrift

Diethyl ethoxymethylmalonate (37.8 mL, 187 mmol) and m-toluidine (20.0 mL, 187 mmol) were combined and heated at 100° C. for about 3 hours. The reaction mixture was allowed to cool to ambient temperature and it solidified. Dowtherm A (350 mL) was added and the reaction mixture was heated at reflux for about 30 minutes. The reaction mixture was allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration, rinsed with acetone and dried to provide 33 g of ethyl 4-hydroxy-7-methyl-3-quinolinecarboxylate as a tan powder.

Quelle