Selenium Dioxide → Ethyl 2-(6-formamidopyridin-2-yl)glyoxylate

HRID 1982701Notes

Reaction equation

HRID 1982701 reaction equation
[CH:1]([NH:3][C:4]1[N:9]=[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2].[Se](=O)=[O:17]>O1CCOCC1>[CH:1]([NH:3][C:4]1[N:9]=[C:8]([C:10](=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 13060164HCID 13060164, compound

Product 1

HCID 13060174Ethyl 2-(6-formamidopyridin-2-yl)glyoxylateYield 51.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of ethyl 2-(6-formamidopyridin-2-yl)acetate (26 g.) in dioxane (260 ml.) was added selenium dioxide (16.65 g.) in small portions at 85° to 90° C. over one hour and stirred at the same temperature for one hour. After cooling the resultant solution the dioxane layer was separated and concentrated under reduced pressure and then the residue was dissolved in ethyl acetate. The solution was washed with water, dried over magnesium sulfate and treated with activated charcoal and then concentrated under reduced pressure. The residue was triturated with diethyl ether to give ethyl 2-(6-formamidopyridin-2-yl)glyoxylate (14.3 g.), mp. 124° to 126° C.

Workup

  1. customwas separated
  2. concentrationconcentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated charcoal
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c4b5dd1362e14e08985d7f3cb066435a
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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