4-Picoline N-oxide → 2-Cyano-4-methylpyridine

HRID 52353ノート

反応式

HRID 52353 の反応式
[N+:1]1([O-])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.C[Si]([C:13]#[N:14])(C)C.N12CCCN=C1CCCCC2>C1COCC1>[C:13]([C:2]1[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][N:1]=1)#[N:14]

参加物

5

反応物 3

HCID 138574-Picoline N-oxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82115Trimethylsilyl cyanide

生成物 1

HCID 887392-Cyano-4-methylpyridine収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a suspension of 4-picoline N-oxide (13.64 g, 0.124 mole) in 82 ml of THF, under an inert atmosphere, was added trimethylsilyl cyanide (20.1 ml, 0.15 mole) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (4.4 ml, 0.028 mole). After stirring at 25 ° C. for 12 hours, the reaction mixture was heated to reflux. After 4.5 hours, the solvent was removed under reduced pressure and the crude sample was eluted with methylene chloride through a pad of Florisil®. The solvent was removed under reduced pressure to provide (8.7 g, 60%) of 2-cyano-4-methyl pyridine, a white crystalline solid: mp 88°-89 ° C. Anal. Calc'd. for C7H6N2 : C, 71.17; H, 5.12; N, 23.71. Found: C, 70.71; H, 5.16; N, 23.44.

後処理

  1. temperaturethe reaction mixture was heated to reflux
  2. waitAfter 4.5 hours
  3. customthe solvent was removed under reduced pressure
  4. washthe crude sample was eluted with methylene chloride through a pad of Florisil®
  5. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-918e91be1836408a8f0f1d4926cfa81f
出典データセット
uspto-grants-1997_04
特許番号
US05616601

反応ノート

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