2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Acetyl-7-(benzyloxy)quinolin-2(1H)-one

HRID 1867323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867323
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[C:15]([C:18]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][C:22](=[O:36])[NH:23]2)(=[O:17])[CH3:16]>O1CCOCC1>[C:15]([C:18]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22](=[O:36])[NH:23]2)(=[O:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 210728505-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one

Produkt 1

HCID 210728495-Acetyl-7-(benzyloxy)quinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

DDQ (15.0 g, 66.08 mmol) is added to a suspension of 5-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one (13.0 g, 44.02 mmol) in dioxane (130 mL) and the mixture is refluxed for 30 minutes. The reaction mixture is cooled to ambient temperature and stirred for a further 2 hours. The precipitate formed is filtered off, washed with dioxane (2×20 mL) and dissolved in dichloromethane/methanol (9:1, 600 mL). The organic phase is washed with sodium bicarbonate solution (2×100 mL), dried with sodium sulfate, and evaporated down. The residue is stirred with methanol, the precipitate formed is filtered off and dried. Yield: 8.3 g (64%); mass spectroscopy: [M+H]+=294.

Aufarbeitung

  1. temperaturethe mixture is refluxed for 30 minutes
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with dioxane (2×20 mL)
  5. dissolutiondissolved in dichloromethane/methanol (9:1, 600 mL)
  6. washThe organic phase is washed with sodium bicarbonate solution (2×100 mL)
  7. dry with materialdried with sodium sulfate
  8. customevaporated down
  9. stirringThe residue is stirred with methanol
  10. customthe precipitate formed
  11. filtrationis filtered off
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c105ffdbecfc4f008cab3e6217d4e611
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632834B2

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