Gramine → Indole-3-acetonitrile

HRID 751506

反応式

HRID 751506 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10]N(C)C)=[CH:2]1.[C-:14]#[N:15].[Na+]>CS(C)=O.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:14]#[N:15])=[CH:2]1

参加物

5

反応物 2

HCID 6890GramineHCID 8929Sodium Cyanide

生成物 1

HCID 351795Indole-3-acetonitrile収率 153.7%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
80 °C

実験手順

Dissolve a mixture of the (1H-Indol-3-ylmethyl)-dimethylamine (3.54 mmol), sodium cyanide (0.500 g, 10.62 mmol), and ethyl acetate (1.7 mL, 17.7 mmol) in dry dimethyl sulfoxide (12 mL) and heat to 80° C. under nitrogen for 3 h. Cool the reaction mixture to room temperature, dilute with ethyl acetate (150 mL), and wash with water (50 mL), Dry the organic layer over anhydrous magnesium sulfate, and remove the solvent in vacuo to yield (1H-indol-3-yl)-acetonitrile 0.850 g (96%).

後処理

  1. dissolutionDissolve
  2. temperatureCool the reaction mixture to room temperature
  3. washwash with water (50 mL)
  4. dry with materialDry the organic layer over anhydrous magnesium sulfate
  5. customremove the solvent in vacuo

出典と根拠

ORDレコード
ord-e24cc133e6be4736953ff22be97bfd37
出典データセット
uspto-grants-2008_07
特許番号
US07405305B2

関連ノート

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