2-Methyl-1H-indole-4-carbonitrile → (2-methyl-1H-indol-4-yl)methanamine

HRID 475115Notes

Reaction equation

HRID 475115 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[C:9]=2[CH:10]=1>N.CO.[Ni]>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([CH2:11][NH2:12])[CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 695458182-Methyl-1H-indole-4-carbonitrile

Product 1

HCID 69545547(2-methyl-1H-indol-4-yl)methanamineYield 95.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a solution of 2-methyl-1H-indole-4-carbonitrile (408 mg, 2.61 mmol) in NH3/MeOH (7 M, 20 mL) was added Raney nickel (100 mg). The mixture was stirred under hydrogen at 1 atmosphere at RT for 3 h. The mixture was filtered with Celite® and the filtrate was concentrated in vacuo to afford (2-methyl-1H-indol-4-yl)methanamine (105) as a yellow solid (398 mg, 95.1%). MS (ESI): m/z=144.3 [M−16]+.

Workup

  1. filtrationThe mixture was filtered with Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-693478032d8747fe94ade8ef97ca19b7
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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