Glyoxal → Quinoxaline, 6-nitro-

HRID 1772004

Reaction equation

HRID 1772004 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:11])[C:7]([NH2:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH:12](=O)[CH:13]=O>CCO>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[N:10]=[CH:13][CH:12]=[N:11]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 96029Quinoxaline, 6-nitro-Yield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-nitrobenzene-1,2-diamine (15.3 g, 0.1 mol) and oxalaldehyde (40% in water, 17.4 g, 0.12 mol) in EtOH (150 mL) was stirred at reflux for 16 h. The mixture was then filtered, and the solid was collected to give 6-nitroquinoxaline as a yellow solid (17.0 g, yield 97%). ESI MS: m/z 176.0 [M+H]+.

Workup

  1. temperatureat reflux for 16 h
  2. filtrationThe mixture was then filtered
  3. customthe solid was collected

Sources & evidence

ORD record
ord-cc9071194f8f47d59f94dee23856f614
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Linked notes

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