m-Chloroperbenzoic acid → 2-Cyano-3-methylpyridine 1-oxide

HRID 1799551ノート

反応式

HRID 1799551 の反応式
[CH3:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-:18])[C:3]=1[C:8]#[N:9]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 8199283-Methylpyridine-2-carbonitrile

生成物 1

HCID 450798222-Cyano-3-methylpyridine 1-oxide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-Methylpyridine-2-carbonitrile (10 g, 85 mmol) was taken up in DCM (180 mL) and mCPBA (20.9 g, 93 mmol) was added. The resulting mixture was stirred at room temperature overnight. Additional mcpba (9.49 g, 42 mmol) was added and stirring continued at room temperature for 24 hours. Saturated aqueous NaHCO3 and the resulting mixture was extracted with EtOAc (3×), followed by 20% MeOH—CHCl3 (2×). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-20% MeOH/EtOAc) gave the title compound as a white solid.

後処理

  1. additionAdditional mcpba (9.49 g, 42 mmol) was added
  2. stirringstirring
  3. waitcontinued at room temperature for 24 hours
  4. extractionSaturated aqueous NaHCO3 and the resulting mixture was extracted with EtOAc (3×)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by silica gel chromatography (0-20% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-735702f7157143a9901ec02472c14caa
出典データセット
uspto-grants-2013_01
特許番号
US08344144B2

反応ノート

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