O-Phenylenediamine → 2-(4-Hydroxy-3-methoxy-5-nitrophenyl)quinoxaline

HRID 274465

Reaktionsgleichung

Reaktionsgleichung von HRID 274465
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([O:15][CH3:16])[CH:6]=1)=O.[C:17]1([NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23].C([O-])(=O)C.[Na+]>CO>[OH:14][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([C:3]2[CH:2]=[N:24][C:17]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:23]=2)=[CH:6][C:7]=1[O:15][CH3:16]

Komponenten

5

Edukt 3

HCID 7243O-PhenylenediamineHCID 517045Sodium AcetateHCID 144509832-Bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone

Produkt 1

HCID 1356653242-(4-Hydroxy-3-methoxy-5-nitrophenyl)quinoxaline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

ada) A suspension of 14.5 g of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone and 5.41 g of 1,2-phenylenediamine in 350 ml of methanol is treated with 4.92 g of sodium acetate and the mixture is heated to boiling under reflux for 22 hours. The reaction mixture is then evaporated, the residue is dissolved in methylene chloride, this solution is washed four times with water, dried over sodium sulfate, filtered and evaporated. There is obtained 2-(4-hydroxy-3-methoxy-5-nitrophenyl)quinoxaline of m.p. 195°-197° (from methylene chloride/methanol).

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 22 hours
  3. customThe reaction mixture is then evaporated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. washthis solution is washed four times with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e6c00635e9fa49eabf0aeab3dc375b79
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389653

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