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

HRID 52353노트

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HRID 52353 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 887392-Cyano-4-methylpyridine수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-918e91be1836408a8f0f1d4926cfa81f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616601

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