Glyoxal → 5-Quinoxalinol

HRID 2374155Notes

Reaction equation

HRID 2374155 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH:10](=O)[CH:11]=O>C(O)(=O)C.C([O-])(=O)C.[Na+].O>[N:8]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([OH:9])[C:2]=2[N:1]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 7860GlyoxalHCID 5799372,3-Diaminophenol

Product 1

HCID 1356902745-Quinoxalinol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 517045Sodium AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2,3-Diaminophenol (2 g) in 10 ml acetic acid and 20 ml 4M sodium acetate and a solution of oxalaldehyde (4.8 g) dissolved in 20 ml water were combined and the resulting mixture was heated at 60° C. for 1.5 h. After cooling to RT water (100 ml) was added and the mixture extracted with EtOAc. The organic layer was dried over Na2SO4, and concentrated to give quinoxalin-5-ol. MS (ESI+) for m/z 147 [M+H]+.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bf9fa961e2814090b734943dcbfe8b35
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Reaction notes

Loading…