Selenium Dioxide → HCID 17974702, compound

HRID 900747Notes

Reaction equation

HRID 900747 reaction equation
[Se](=O)=[O:2].[Cl:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[CH3:15])=[CH:12][CH:11]=[CH:10][CH:9]=2>O1CCOCC1.O>[Cl:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[CH:15]=[O:2])=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 92597Quinoline, 3-chloro-4-methyl-

Product 1

HCID 17974702HCID 17974702, compoundYield 37.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of selenium dioxide (1.90 g) in 1,4-dioxan (5 ml) and water (1.2 ml) was added dropwise over 15 min to a stirred solution of 3-chloro-4-methylquinoline (2.91 g) in 1,4-dioxan (10 ml) at 60-70° C. The mixture was heated at reflux for 6 h, allowed to warm to room temperature, then concentrated in vacuo. The residue was purified by column chromatography (SiO2), eluting with dichloromethane to 5% methanol in dichloromethane by a stepwise gradient, to give the sub-title compound as a yellow solid (1.19 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (SiO2)
  5. washeluting with dichloromethane to 5% methanol in dichloromethane by a stepwise gradient

Sources & evidence

ORD record
ord-ed0566c55bec47bf9f1bf05e43d9d6bf
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Reaction notes

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