Selenium Dioxide → 3-Nitropicolinaldehyde

HRID 473402

Reaction equation

HRID 473402 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>[N+:8]([C:7]1[C:2]([CH:1]=[O:12])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 3293602-Methyl-3-nitropyridine

Product 1

HCID 3293613-Nitropicolinaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Methyl-3-nitropyridine (24 g, 173.91 mmol) was dissolved in 1,4-dioxane (500 mL) and to the mixture was added selenium dioxide (23 g, 208.7 mmol) and the mixture was heated under reflux for 16 h. After completion of reaction, the mixture was cooled to rt and filtered through Celite™ and the filtrate was concentrated under reduced pressure to give thick oily mass. The oily mass was purified by silical gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 3-nitro-2-pyridinecarbaldehyde as an off white solid: 1H-NMR (CDCl3) δ: 7.7 (m, 1H), 8.3 (d, 1H), 9.0 (d, 1H), 10.3 (s, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 h
  3. customAfter completion of reaction
  4. filtrationfiltered through Celite™
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give thick oily mass
  7. customThe oily mass was purified by silical gel column chromatography

Sources & evidence

ORD record
ord-6125dbff90ba4f408de676406cbf1884
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Linked notes

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