1,4-Dioxane → Methyl 2-formylquinoline-7-carboxylate

HRID 338861Notes

Reaction equation

HRID 338861 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=2)[N:3]=1.[O:16]1CCOCC1>O>[CH:1]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=2)[N:3]=1)=[O:16]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 67978375Methyl 2-methylquinoline-7-carboxylate

Product 1

HCID 86707420Methyl 2-formylquinoline-7-carboxylateYield 70.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-methylquinoline-7-carboxylate (0.99 g, 4.92 mmol) in dioxane (60 mL) and water (0.6 mL) was added SeO2 (0.66 g, 5.90 mmol) and the mixture was stirred at reflux for 2 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:4 hexane/ethyl acetate) to give methyl 2-formylquinoline-7-carboxylate (0.75 g, 70.8%) as a solid.

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solid was removed by filtration
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel (1:4 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c2d880793db94ae6b978fb0d7ffb8609
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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