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

HRID 510477ノート

反応式

HRID 510477 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

HCID 30151966-Methyl-5-nitropyridine-2-carbaldehyde収率 37.4%

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-9caca7fe79674456bdb2f797ae4b1b15
出典データセット
uspto-grants-2015_08
特許番号
US09096614B2

反応ノート

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