Selenium Dioxide → HCID 21847014, compound

HRID 619682Notes

Reaction equation

HRID 619682 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Se](=O)=[O:18]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 103990241-(4-Chloro-phenyl)-2-pyridin-4-YL-ethanone

Product 1

HCID 21847014HCID 21847014, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 25 g of 1-(4-chlorophenyl)-2-pyridin-4-yl-ethanone in 285 ml of dioxan was treated with 20 g of selenium dioxide. The mixture was stirred at 100° C. for 1 hour and filtered. The solvent was evaporated and the residue was dissolved in dichloromethane. The solution was washed three times with water, dried over anhydrous magnesium sulphate and evaporated. The residue was dissolved in ethyl acetate, the solution was filtered over silica gel and evaporated to yield 23.7 g of 1-(4-chlorophenyl)-2-pyridin-4-yl-ethanedione, m.p. 119-120° C.

Workup

  1. filtrationfiltered
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThe solution was washed three times with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. filtrationthe solution was filtered over silica gel
  9. customevaporated

Sources & evidence

ORD record
ord-9a69dc3e69de49eaa72b899978a8486c
Source dataset
uspto-grants-1999_09
Patent number
US05959113

Reaction notes

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