1,4-Dioxane → 6, 7-Dimethoxy-2-quinoxaline carboxaldehyde

HRID 1018498Notes

Reaction equation

HRID 1018498 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:14][CH3:15])=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[O:16]1CCOCC1>>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:14][CH3:15])[N:3]=[C:2]([CH:1]=[O:16])[CH:11]=[N:10]2

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 1325416,7-Dimethoxy-2-methylquinoxaline

Product 1

HCID 225731216, 7-Dimethoxy-2-quinoxaline carboxaldehydeYield 73%

Conditions

Temperature
100 °C

Procedure

To a reaction flask under argon is added 1,4-dioxane (20 mL), 2-methyl-6,7-dimethoxyquinoxaline (1.09 g. 5.3 mmol) and SeO2 (1.8 g. 16 mmol). The mixture is heated to 100° C. for 2 hours 45 minutes, cooled, and filtered through Celite. The pad is washed with portions of EtOAc and CH2Cl2. The resulting solution is concentrated, taken up in MeOH/CH2Cl2, loaded onto a silica gel column, and chromatographed (30% EtOAc/CH2Cl2) to provide an off-white solid (73% yield).

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite
  3. washThe pad is washed with portions of EtOAc and CH2Cl2
  4. concentrationThe resulting solution is concentrated
  5. customchromatographed (30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-71d2bc76f7034d38bcbcd0117002e89a
Source dataset
uspto-grants-2002_11
Patent number
US06482834B2

Reaction notes

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