Acetic Anhydride → (Z)-1,1'-(4-(methoxymethylene)-3-oxo-3,4-dihydrocinnoline-1,2-diyl)diethanone

HRID 2236574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236574
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6](=[O:14])[N:5]1[C:15](=[O:17])[CH3:16])(=[O:3])[CH3:2].[C:18]([O:21][C:22](=O)C)(=O)C.COC(OC)OC>CN(C)C=O>[CH3:18][O:21]/[CH:22]=[C:7]1\[C:6](=[O:14])[N:5]([C:15](=[O:17])[CH3:16])[N:4]([C:1](=[O:3])[CH3:2])[C:13]2[C:8]\1=[CH:9][CH:10]=[CH:11][CH:12]=2

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 218292321,2-diacetyl-1,4-dihydro-3(2H)cinnolinone

Produkt 1

HCID 59300145(Z)-1,1'-(4-(methoxymethylene)-3-oxo-3,4-dihydrocinnoline-1,2-diyl)diethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1,2-diacetyl-1,4-dihydro-3(2H)cinnolinone (0.34 g, 1.5 mmol) in dimethylformamide (3.6 mL) is added acetic anhydride (5 mL), followed by trimethylorthoformate (0.64 mL). The mixture is heated at reflux for 12 hours. After cooling to room temperature, the mixture is purified by semi-preparative reverse-phase HPLC, employing a gradient elution from 5% acetonitrile in water with 0.1% trifluoroacetic acid to 100% acetonitrile over 60 minutes. The desired fractions were concentrated under reduced pressure to afford 0.18 g of (Z)-1,1′-(4-(methoxymethylene)-3-oxo-3,4-dihydrocinnoline-1,2-diyl)diethanone.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 12 hours
  3. customthe mixture is purified by semi-preparative reverse-phase HPLC
  4. washa gradient elution from 5% acetonitrile in water with 0.1% trifluoroacetic acid to 100% acetonitrile over 60 minutes
  5. concentrationThe desired fractions were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-87dadd7f3fac4fceb58d7727d56f23d1
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713994B2

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