Water → 5-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile

HRID 534009

反応式

HRID 534009 の反応式
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[H-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.O>CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]([O:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=2)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 707322,6-Dimethyl-3-pyridinolHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

生成物 1

HCID 674864525-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile収率 101.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a 0° C. solution of 2,6-dimethylpyridin-3-ol (10 g, 81.2 mmol) in DMF (50 ml) was added sodium hydride (60% dispersion in oil, 3.4 g, 85 mmol). After 15 minutes, 5-bromo-3-nitropicolinonitrile (18.5 g, 81 mmol) was added and the mixture was allowed to warm slowly to ambient temperature. The reaction mixture was slowly added to 500 mL of rapidly stirring water. A light red solid formed and then the material formed a gum. The gum was extracted into ethyl acetate, and the organics washed with brine, dried over MgSO4 and concentrated in vacuo to afford 5-bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile (25 g, 82 mmol, 101% yield).

後処理

  1. customA light red solid formed
  2. customthe material formed a gum
  3. extractionThe gum was extracted into ethyl acetate
  4. washthe organics washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d3ebc3b23e2d4d389e88503e7fd5fbc1
出典データセット
uspto-grants-2014_10
特許番号
US08853409B2

関連ノート

読み込み中…