Selenium Dioxide → HCID 83813717, compound

HRID 338892Notes

Reaction equation

HRID 338892 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]#[N:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Se](=O)=[O:15]>O1CCOCC1.O>[CH:1]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:12]#[N:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[O:15]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 336982272-Methylquinoline-8-carbonitrile

Product 1

HCID 83813717HCID 83813717, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-methylquinoline-8-carbonitrile (1.70 g, 10.1 mmol) in 1,4-dioxane (50 mL) and water (1 mL), was added selenium dioxide (2.80 g, 25.3 mmol) and the resulting mixture heated at reflux for 7 hours. After cooling to ambient temperature, the solids formed were removed by filtration through a pad of Celite® and washed with 1:1 mixture of ethyl acetate/dichloromethane (50 mL). The filtrate was concentrated under reduced pressure and the residue obtained purified by column chromatography (Biotage, 40M; 1% MeOH: dichloromethane) to give 2-formylquinoline-8-carbonitrile (1.51 g, 82%).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 7 hours
  3. customthe solids formed
  4. customwere removed by filtration through a pad of Celite®
  5. washwashed with 1:1 mixture of ethyl acetate/dichloromethane (50 mL)
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue obtained
  8. custompurified by column chromatography (Biotage, 40M; 1% MeOH: dichloromethane)

Sources & evidence

ORD record
ord-2a7f8922ef0c463eb530eda9203ad697
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…