Glyoxal → 6-Bromoquinoxaline

HRID 2176536Notes

Reaction equation

HRID 2176536 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH:10](=O)[CH:11]=O>CCO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]=[CH:11][CH:10]=[N:9]2

Participants

5

Reactant 2

HCID 7860GlyoxalHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 6109396-Bromoquinoxaline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-bromobenzene-1,2-diamine (4.0 g, 21 mmol) in 60 mL of EtOH was added 40% glyoxal aldehyde (4.1 ml, 32 mmol) solution in water. The resulting mixture was refluxed for 10 hours. The mixture was concentrated in vacuo and the residue was diluted in 100 mL of EtOAc. The organic solution was washed with 40 mL of satd. NaHCO3 and 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silca gel column chromatography (5% EtOAc/hex to EtOAC) to give light yellow solid 6-bromoquinoxaline. MS (ESI, pos. ion) m/z: 208.9 (M+1).

Workup

  1. temperatureThe resulting mixture was refluxed for 10 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe residue was diluted in 100 mL of EtOAc
  4. washThe organic solution was washed with 40 mL of satd
  5. dry with materialNaHCO3 and 40 mL of brine, dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silca gel column chromatography (5% EtOAc/hex to EtOAC)

Sources & evidence

ORD record
ord-e303c072bc0d497986a990d129c5bc93
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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