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

HRID 1811588

Reaction equation

HRID 1811588 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 75%

Procedure

A solution of 2,6-dimethyl-3-nitropyridine (50 g, 329 mmol) and SeO2 (5.02 g, 27.9 mmol) in dioxane (500 mL) was heated at reflux for 16 hours. The solution was filtered, the solvent removed and the residue purified by column chromatography directly (20% EtOAc/hexanes). The material was recrystalized from ethyl acetate to give 41 g of 6-methyl-5-nitropicolinaldehyde (41 g, 75%), a pale yellow solid; 1HNMR (CDCl3, 400 MHz) δ 2.94 (s, 3H), 7.98 (d, J=8.34, 1H), 8.41 (d, J=8.34, 1H), 10.09 (s, 1H). Exact mass calculated for C7H6N2O3: 166.04. found: 167.12 MS m/z (MH+).

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationThe solution was filtered
  3. customthe solvent removed
  4. customthe residue purified by column chromatography directly (20% EtOAc/hexanes)
  5. customThe material was recrystalized from ethyl acetate

Sources & evidence

ORD record
ord-c7a49e4f5aea4c2ca1c8191e028b25a2
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Linked notes

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