Water → HCID 15007049, compound

HRID 1613942Notes

Reaction equation

HRID 1613942 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]([O:13][C:14](=[O:16])[CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Se](=O)=[O:18].O>O1CCOCC1>[CH:1]([C:2]1[C:11]([CH3:12])=[C:10]([O:13][C:14](=[O:16])[CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 15007064HCID 15007064, compound

Product 1

HCID 15007049HCID 15007049, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.30 g (20.0 mmols) of 2,3-dimethyl-4-acetoxyquinoline, 2.44 g (22.0 mmols) of selenium dioxide, 8 ml of water and 80 ml 1,4-dioxane was refluxed for 3 hours. The solvent was distilled off under reduced pressure, after which 100 ml of chloroform was added, followed by washing with a saturated sodium hydrogencarbonate aqueous solution and then with water, and drying with sodium sulfate. The solvent was distilled off under reduced pressure and the resultant crude product was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=10:1) to obtain 2.40 g (yield 52%) of 2-formyl-3-methyl-4-acetoxyquinoline.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionafter which 100 ml of chloroform was added
  3. washby washing with a saturated sodium hydrogencarbonate aqueous solution
  4. dry with materialwith water, and drying with sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant crude product was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2ed5f8f466d84e64a8a1cd8bdbc0b777
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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