Selenium Dioxide → 3-Nitropicolinaldehyde

HRID 1932287

Reaction equation

HRID 1932287 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Se](=O)=[O:12]>O1CCOCC1>[CH:1]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:12]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 3293602-Methyl-3-nitropyridine

Product 1

HCID 3293613-NitropicolinaldehydeYield 116.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-methyl-3-nitropyridine (10.155 g, 72.46 mmol) prepared in Step 1 of Preparation 1 and selenium dioxide (8.84 g, 79.71 mmol) in 1,4-dioxane (80 ml) was refluxed for 2 days. The reaction mixture was cooled to room temperature, filtered, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/2, v/v) to give 12.8 g of the titled compound as red oil.

Workup

  1. temperaturewas refluxed for 2 days
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/2, v/v)

Sources & evidence

ORD record
ord-d3c0430ac2da4b19b551b6fc52fdaab1
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Linked notes

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