Selenium Dioxide → 3-Chloro-6'-formyl-[2,3]bipyridyl-5-carboxylic acid methyl ester

HRID 2089116Notes

Reaction equation

HRID 2089116 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:18])[C:8]([C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[N:9][CH:10]=1)=[O:4].[Se](=O)=[O:20]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:18])[C:8]([C:11]2[CH:12]=[N:13][C:14]([CH:17]=[O:20])=[CH:15][CH:16]=2)=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 57825687Methyl 3-chloro-6'-methyl[2,3'-bipyridine]-5-carboxylate

Product 1

HCID 578256963-Chloro-6'-formyl-[2,3]bipyridyl-5-carboxylic acid methyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.6 g of 3-chloro-6′-methyl-[2,3′]bipyridyl-5-carboxylic acid methyl ester (12) (2.3 mmol) prepared in Example 8 was dissolved in 10 mL of 1,4-dioxane, and 0.75 g of selenium dioxide (6.9 mmol) was added thereto. The mixture was refluxed under heating and stirring for 18 hours, and cooled to room temperature. The mixture was concentrated under reduced pressure, and then dissolved in ethyl acetate to be washed with water. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=10/1) to obtain 0.51 g of yellow crystal, 3-chloro-6′-formyl-[2,3′]bipyridyl-5-carboxylic acid methyl ester (yield 81%)

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutiondissolved in ethyl acetate
  5. washto be washed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was separated by column chromatography (eluting solvent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-a7daaeda3d7f4a9fadb7b7cfca1faf3a
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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