Ammonia → 1-(1H-indol-6-yl)methanamine

HRID 1058375Notes

Reaction equation

HRID 1058375 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[CH:2]1.N>C(O)C.[Ni]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][NH2:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 851461H-indole-6-carbonitrile

Product 1

HCID 172211011-(1H-indol-6-yl)methanamineYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1H-indole-6-carbonitrile (prepared by the literature procedure: Batcho, A. D.; Leimgruber, W. Organic Syntheses 1985, 63, 214-225; 1.50 g, 10.6 mmol), Raney an nickel and concentrated aqueous ammonia (4 mL) in ethanol (50 mL) was hydrogenated at atmospheric pressure overnight. The mixture was filtered through Celite® and the filter cake was washed thoroughly with ethanol, while taking care not to allow the catalyst to become dry. The combined filtrates were concentrated to give 1H-indole-6-methanamine (1.50 g, 97% yield).

Workup

  1. customprepared by the literature procedure
  2. customwas hydrogenated at atmospheric pressure overnight
  3. filtrationThe mixture was filtered through Celite®
  4. washthe filter cake was washed thoroughly with ethanol
  5. customto become dry
  6. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-7fd80de3ab174076900b371e7130531a
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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