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

HRID 1811588

反応式

HRID 1811588 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 75%

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-c7a49e4f5aea4c2ca1c8191e028b25a2
出典データセット
uspto-grants-2013_01
特許番号
US08362248B2

関連ノート

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