Selenium Dioxide → 3-Nitropicolinaldehyde

HRID 473402ノート

反応式

HRID 473402 の反応式
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Se](=O)=[O:12]>O1CCOCC1>[N+:8]([C:7]1[C:2]([CH:1]=[O:12])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

参加物

4

反応物 2

HCID 24007Selenium DioxideHCID 3293602-Methyl-3-nitropyridine

生成物 1

HCID 3293613-Nitropicolinaldehyde

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

2-Methyl-3-nitropyridine (24 g, 173.91 mmol) was dissolved in 1,4-dioxane (500 mL) and to the mixture was added selenium dioxide (23 g, 208.7 mmol) and the mixture was heated under reflux for 16 h. After completion of reaction, the mixture was cooled to rt and filtered through Celite™ and the filtrate was concentrated under reduced pressure to give thick oily mass. The oily mass was purified by silical gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 3-nitro-2-pyridinecarbaldehyde as an off white solid: 1H-NMR (CDCl3) δ: 7.7 (m, 1H), 8.3 (d, 1H), 9.0 (d, 1H), 10.3 (s, 1H).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 h
  3. customAfter completion of reaction
  4. filtrationfiltered through Celite™
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give thick oily mass
  7. customThe oily mass was purified by silical gel column chromatography

出典と根拠

ORDレコード
ord-6125dbff90ba4f408de676406cbf1884
出典データセット
uspto-grants-2014_01
特許番号
US08633313B2

反応ノート

読み込み中…