1,4-Dioxane → 6-Methyl-5-nitropyridine-2-carbaldehyde

HRID 510477

Reaction equation

HRID 510477 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.[O:12]1CCOCC1>>[CH3:1][C:2]1[N:3]=[C:4]([CH:11]=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 849582,6-Dimethyl-3-nitropyridine

Product 1

HCID 30151966-Methyl-5-nitropyridine-2-carbaldehydeYield 37.4%

Procedure

A solution of 2,6-dimethyl-3-nitropyridine (1.5 g, 9.85 mmol) and SeO2 (1.4 g, 12.81 mmol) in 1,4-dioxane (15 mL) was heated at reflux for 16 h. The reaction mixture was then filtered through Celite and the solvent was evaporated. The crude material obtained was purified by column chromatography (silica: 100-200 mesh, EtOAc:hexane 20-25%) to afford the title compound (0.61 g, 37.4%). δH (CDCl3) 10.09 (s, 1H), 8.39 (d, J=8.3 Hz, 1H), 7.97 (d, J=8.3 Hz, 1H), 2.94 (s, 3H).

Workup

  1. temperatureat reflux for 16 h
  2. filtrationThe reaction mixture was then filtered through Celite
  3. customthe solvent was evaporated
  4. customThe crude material obtained
  5. customwas purified by column chromatography (silica: 100-200 mesh, EtOAc:hexane 20-25%)

Sources & evidence

ORD record
ord-9caca7fe79674456bdb2f797ae4b1b15
Source dataset
uspto-grants-2015_08
Patent number
US09096614B2

Linked notes

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