Butanedione → 2,3-Dimethyl-6-nitroquinoxaline

HRID 1719494Notes

Reaction equation

HRID 1719494 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[CH3:12][C:13](=O)[C:14](=O)[CH3:15]>>[CH3:12][C:13]1[C:14]([CH3:15])=[N:11][C:6]2[C:7](=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

3

Reactant 2

HCID 650ButanedioneHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 6089992,3-Dimethyl-6-nitroquinoxaline

Procedure

A stirred mixture of 4-nitro-o-phenylenediamine (Fairmont) (105 g, 0.69 mole) and 2,3-butanedione (Aldrich) (59 g, 0.69 mole) in 1.5 L of SDA-32 was heated at reflux for 4 hours. The reaction mixture was let stand at room temperature overnight. The crystallized intermediate was chilled and collected to give after ether wash 62.9 g (44.9%) of known solid. The intermediate was used without further purification in step B.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customat room temperature
  4. customovernight
  5. temperatureThe crystallized intermediate was chilled
  6. customcollected
  7. customto give after ether
  8. washwash 62.9 g (44.9%) of known solid
  9. customThe intermediate was used without further purification in step B

Sources & evidence

ORD record
ord-9a6dd80caf2a4a3691dea845ae3f7f9a
Source dataset
uspto-grants-1985_09
Patent number
US04540693

Reaction notes

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