Ethyl oxoacetate → 7-Methoxy-1,2-dihydroquinoxalin-2-one

HRID 250035

Reaktionsgleichung

Reaktionsgleichung von HRID 250035
O=C[C:3]([O:5][CH2:6][CH3:7])=O.COC1C=C(N)C(N)=CC=1.CO[C:20]1[CH:21]=[C:22]2[C:27](=CC=1)[NH:26][C:25](=[O:30])[CH:24]=[N:23]2>C1(C)C=CC=CC=1.C(O)C>[CH3:3][O:5][C:6]1[CH:7]=[C:27]2[C:22]([N:23]=[CH:24][C:25](=[O:30])[NH:26]2)=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 70211Ethyl oxoacetateHCID 1534044-Methoxy-o-phenylenediamineHCID 134377076-Methoxyquinoxalin-2(1H)-one

Produkt 1

HCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-oneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 50% solution of ethyl 2-oxoacetate (18.47 mL, 93 mmol) in toluene was added to a solution of 4-methoxybenzene-1,2-diamine (10.73 g, 78 mmol) in ethanol (100 mL) at ambient temperature and the reaction was refluxed for 2 h. The reaction was concentrated in vacuo and crystallized from ethanol to afford a mixture of 6-methoxyquinoxalin-2(1H)-one and 7-methoxyquinoxalin-2(1H)-one (5.73 g, 32.50 mmol, 42% yield). MS (LC/MS) R.T.=0.68; [M+H]+=177.10.

Aufarbeitung

  1. temperaturethe reaction was refluxed for 2 h
  2. concentrationThe reaction was concentrated in vacuo
  3. customcrystallized from ethanol
  4. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-70338d01ba6b4573bff4ffaea4d8535f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863291B2

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