4,5-Dinitrobenzene-1,2-diamine → 2,3-Diethyl-6,7-dinitroquinoxaline

HRID 628927Notes

Reaction equation

HRID 628927 reaction equation
[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([NH2:13])=[C:6]([NH2:14])[CH:5]=1)([O-:3])=[O:2]>C(O)C>[CH2:9]([C:4]1[C:5]([CH2:6][CH3:7])=[N:14][C:6]2[C:7](=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:13]=1)[CH3:8]

Participants

3

Reactant 1

HCID 44419034,5-Dinitrobenzene-1,2-diamine

Product 1

HCID 1182747772,3-Diethyl-6,7-dinitroquinoxalineYield 144.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,5-Dinitro-1,2-phenylenediamine (1000 mg, 5.0 mmol), 3,4-hexadione (685 mg, 6.0 mmol) and ethanol (50 mL) were mixed in a round bottom flask equipped with a condenser. The reaction mixture was refluxed overnight. The mixture was cooled down to room temperature and ethanol was removed under reduced pressure. It was then extracted with methylene chloride and the organic phase was washed with water and dried over Na2SO4. The product obtained as off-white solid (1000 mg, 72%) was purified by column chromatography.

Workup

  1. customequipped with a condenser
  2. temperatureThe reaction mixture was refluxed overnight
  3. customethanol was removed under reduced pressure
  4. extractionIt was then extracted with methylene chloride
  5. washthe organic phase was washed with water
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-b49b99e3072e47f4a3d490447230b48e
Source dataset
uspto-grants-2016_04
Patent number
US09315477B2

Reaction notes

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