Selenium Dioxide → (R)-7-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde

HRID 338968Notes

Reaction equation

HRID 338968 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH3:17])=[N:14]2)=[CH:9][CH:8]=1)[CH3:5].[Se](=O)=[O:19]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH:17]=[O:19])=[N:14]2)=[CH:9][CH:8]=1)[CH3:5]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 86707484(R)-7-(1-methoxypropan-2-yloxy)-2-methylquinoline

Product 1

HCID 86707485(R)-7-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehydeYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-7-(1-methoxypropan-2-yloxy)-2-methylquinoline (0.22 g, 0.96 mmol) in dioxane (7 mL) and water (0.07 mL) was added selenium dioxide (0.13 g, 1.2 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 (0.11 g, 46%).

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-60683fce0a174197ab659987e053a4bf
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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