Glyoxal → Quinoxaline, 5-nitro-

HRID 513746

Reaktionsgleichung

Reaktionsgleichung von HRID 513746
[CH:1]([CH:3]=O)=O.[N+:5]([C:8]1[C:9]([NH2:15])=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6]>CCO>[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:9]=1[N:15]=[CH:1][CH:3]=[N:14]2)([O-:7])=[O:6]

Komponenten

4

Edukt 2

HCID 7860GlyoxalHCID 43595253-Nitro-1,2-phenylenediamine

Produkt 1

HCID 97512Quinoxaline, 5-nitro-Ausbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Oxaldehyde (40% in water; 1.43 ml, 31.3 mmol) was added to a solution of 3-nitro-o-phenylene-diamine (600 mg, 3.9 mmol) in EtOH (15 ml) and the mixture was heated at 85° C. for 2 h. The solvent was removed in vacuo, the residue was diluted in water and the aqueous phase was extracted with DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent to give the title compound (666 mg, 97%).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted in water
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-aa1fa3bc74884eecb8bf344e5a373036
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

Verknüpfte Notizen

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