Selenium Dioxide → 7-(2-Methoxyethoxy)quinoline-2-carbaldehyde

HRID 338964Notes

Reaction equation

HRID 338964 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH3:16])=[N:13]2)=[CH:8][CH:7]=1.[Se](=O)=[O:18]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH:16]=[O:18])=[N:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 709831307-(2-Methoxyethoxy)-2-methylquinoline

Product 1

HCID 867074817-(2-Methoxyethoxy)quinoline-2-carbaldehydeYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7-(2-methoxyethoxy)-2-methylquinoline (0.16 g, 0.76 mmol) in dioxane (15 mL) and water (0.15 mL) was added selenium dioxide (0.10 g, 0.91 mmol) and the resultant mixture heated at reflux for 2 hours. The cooled reaction mixture was filtered through a plug of Celite® to remove solids, rinsing with dichloromethane. The filtrate was concentrated under reduced pressure and purified by normal phase chromatography on silica gel (10-20% ethyl acetate/hexanes) to afford the title compound (0.12 g, 70%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through a plug of Celite®
  4. customto remove solids
  5. washrinsing with dichloromethane
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by normal phase chromatography on silica gel (10-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2f97171084934d07b8ce9355e2c73a37
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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