Water → 2-Formylnicotinonitrile

HRID 7154

反応式

HRID 7154 の反応式
[C:1]([C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].O.[Se](=O)=[O:12]>O1CCOCC1>[C:1]([C:3]1[C:4]([CH:9]=[O:12])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2]

参加物

5

反応物 3

HCID 962WaterHCID 24007Selenium DioxideHCID 47383082-Methylpyridine-3-carbonitrile

生成物 1

HCID 190294752-Formylnicotinonitrile収率 10%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 3-cyano-2-picoline (166 mg, 1.41 mmol) in dioxane (3 mL) was added water (0.2 mL) and selenium(IV) oxide (228 mg, 2.05 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1 then 1:1) to afford the title compound (18 mg, 10%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.69 (dd, 1H, J=9, 6 Hz), 8.20 (d, 1H, J=9 Hz), 9.00 (d, 1H, J=3 Hz), 10.13 (s, 1H).

後処理

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel (Hexanes/ether, 3:1

出典と根拠

ORDレコード
ord-c91b9e7b100246bd91748a1ae525db65
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

関連ノート

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