1-methyl-1H-indole-5-carbonitrile → (1-methyl-1H-indol-5-yl)methylamine

HRID 475294

Reaction equation

HRID 475294 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1>N.CO.[Ni]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][NH2:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 1

HCID 114125131-methyl-1H-indole-5-carbonitrile

Product 1

HCID 18525752(1-methyl-1H-indol-5-yl)methylamineYield 97.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 294 (800 mg, 5.12 mmol) in 7M ammonia in MeOH (50 mL) was added Raney Ni (2.0 g) and the reaction mixture was stirred vigorously under H2 (1 atm.) atmosphere at RT for 18 h. The reaction mixture was filtered through a pad of Celite® and concentrated in vacuo to afford 800 mg of (1-methyl-1H-indol-5-yl)methanamine (296) as yellow oil: MS (ESI) m/z=144.3 [M-NH2]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd7b3e8fbf3d496f9f47619c07dbacbe
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Linked notes

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