Gramine → Indole-3-acetonitrile

HRID 751506

반응식

HRID 751506 반응식
[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

참가 물질

5

반응물 2

HCID 6890GramineHCID 8929Sodium Cyanide

생성물 1

HCID 351795Indole-3-acetonitrile수율 153.7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e24cc133e6be4736953ff22be97bfd37
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405305B2

연결된 노트

불러오는 중…