Selenium Dioxide → 4-Methyl-3-oxo-3,4-dihydro-quinoxaline-2-carbaldehyde

HRID 493981Notes

Reaction equation

HRID 493981 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[C:3]1=[O:13].[Se](=O)=[O:15]>O1CCOCC1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:12]=[O:15])[C:3]1=[O:13]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 3514221,3-dimethylquinoxalin-2(1H)-one

Product 1

HCID 576824964-Methyl-3-oxo-3,4-dihydro-quinoxaline-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,3-dimethyl-1H-quinoxalin-2-one (1 g) and selenium dioxide (1.33 g, 2.1 eq) in dry dioxane (60 mL) was stirred at reflux under nitrogen for 30 min. After cooling, the dark-brown mixture was concentrated under reduced pressure and the residue was purified by FC (AcOEt) to give the title compound as a yellow solid.

Workup

  1. temperatureat reflux under nitrogen for 30 min
  2. temperatureAfter cooling
  3. concentrationthe dark-brown mixture was concentrated under reduced pressure
  4. customthe residue was purified by FC (AcOEt)

Sources & evidence

ORD record
ord-860b6fcc136d4dc5aca5446ec57df801
Source dataset
uspto-grants-2009_05
Patent number
US07538109B2

Reaction notes

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