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

HRID 1811588

Reaktionsgleichung

Reaktionsgleichung von HRID 1811588
[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]

Komponenten

3

Edukt 2

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

Produkt 1

HCID 30151966-Methyl-5-nitropyridine-2-carbaldehydeAusbeute 75 %

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c7a49e4f5aea4c2ca1c8191e028b25a2
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362248B2

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