Diethyl (ethoxymethylene)malonate → 6-methoxy-7-(2-methoxyethoxy)quinolin-4(1H)-one

HRID 393605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393605
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][O:13][CH3:14].C([O:17][CH:18]=[C:19](C(OCC)=O)[C:20](OCC)=O)C.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:9]=[C:8]2[C:6](=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][O:13][CH3:14])[NH:7][CH:20]=[CH:19][C:18]2=[O:17]

Komponenten

4

Edukt 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7583Diphenyl EtherHCID 108455954-Methoxy-3-(2-methoxyethoxy)aniline

Produkt 1

HCID 106343396-methoxy-7-(2-methoxyethoxy)quinolin-4(1H)-oneAusbeute 8 %

Reaktionsbedingungen

Temperatur
240 °C

Versuchsvorschrift

A solution of 4-methoxy-3-(2-methoxyethoxy)aniline (5 g, 25.3 mmol) and diethyl ethoxymethylenemalonate (6 ml, 30 mmol) was heated at 110° C. for 30 minutes. Phenyl ether (5 ml) was added and the mixture was heated at 240° C. for 6 hours. The mixture was allowed to cool and diluted with petroleum ether. The resulting solid was collected by filtration and purified by reverse phase chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column eluting with acetonitrile/water (40/60) to give 6-methoxy-7-(2-methoxyethoxy)-1,4-dihydroquinolin-4-one (500 mg, 8%).

Aufarbeitung

  1. temperatureto cool
  2. filtrationThe resulting solid was collected by filtration
  3. custompurified by reverse phase chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  4. washeluting with acetonitrile/water (40/60)

Quellen und Nachweise

ORD-Eintrag
ord-e54e8055743f427c9a5296d9d3424d10
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809097B1

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