Gramine → Indole-3-acetonitrile

HRID 751506

Reaction equation

HRID 751506 reaction equation
[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

Participants

5

Reactant 2

HCID 6890GramineHCID 8929Sodium Cyanide

Product 1

HCID 351795Indole-3-acetonitrileYield 153.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-e24cc133e6be4736953ff22be97bfd37
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Linked notes

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