m-Toluidine → Ethyl 7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 393935

Reaktionsgleichung

Reaktionsgleichung von HRID 393935
C(O[CH2:4][CH:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[OH:13][C:11]1[C:22]2[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=2)[N:16]=[CH:4][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Komponenten

4

Edukt 2

HCID 7934m-ToluidineHCID 98702Diethyl (ethoxymethyl)malonate

Produkt 1

HCID 178469524Ethyl 7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for about 30 minutes
  4. temperatureto cool to ambient temperature
  5. customThe resulting precipitate was isolated by filtration
  6. washrinsed with acetone
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-409dc54188c142688eb537344e936c84
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809203B2

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