Selenium Dioxide → Quinoxaline-6-carboxaldehyde

HRID 1854665Notes

Reaction equation

HRID 1854665 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2.[Se](=O)=[O:13]>C(OCC)(=O)C>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:1]=[O:13])=[CH:11][CH:10]=2)[N:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 2425676-Methylquinoxaline

Product 1

HCID 763958Quinoxaline-6-carboxaldehydeYield 64.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-Methylquinoxaline (500 mg, 3.47 mmol) and selenium dioxide (423 mg, 3.81 mmol) in a sealed vessel were stirred at 160° C. for 7 h. After cooled to room temperature, the reaction mixture was dissolved in ethyl acetate. The solution was washed with brine twice, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain the title compound as a pale brown solid (355 mg, 64%).

Workup

  1. washThe solution was washed with brine twice
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40)

Sources & evidence

ORD record
ord-619024aa1c9b402f856585fc57eeb209
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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