Selenium Dioxide → 7-(2-Methoxyethoxy)-8-methylquinoline-2-carbaldehyde

HRID 338923Notes

Reaction equation

HRID 338923 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([CH3:16])=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH3:17])=[N:13]2)=[CH:8][CH:7]=1.[Se](=O)=[O:19]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([CH3:16])=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH:17]=[O:19])=[N:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 709840567-(2-Methoxyethoxy)-2,8-dimethylquinoline

Product 1

HCID 867074527-(2-Methoxyethoxy)-8-methylquinoline-2-carbaldehydeYield 70%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To 7-(2-methoxyethoxy)-2,8-dimethylquinoline (90 mg, 0.39 mmol) in dioxane/water (5 mL/0.5 mL) at ambient temperature was added selenium dioxide (52 mg, 0.47 mmol) and the reaction was heated to reflux for 1 hour. After cooling, the reaction was filtered and the solids washed with DCM. The filtrate was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (SP4, 12M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 7-(2-methoxyethoxy)-8-methylquinoline-2-carbaldehyde (67 mg, 70% yield) as a tan solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe reaction was filtered
  5. washthe solids washed with DCM
  6. dry with materialThe filtrate was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by reverse phase chromatography (SP4, 12M
  10. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-336d486b403c45b0b68eef6e3a4c5de1
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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