Glyoxal → Quinoxaline, 5-nitro-

HRID 513746

Reaction equation

HRID 513746 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 97512Quinoxaline, 5-nitro-Yield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-aa1fa3bc74884eecb8bf344e5a373036
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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