5-methyl-1H-indole-4-carbonitrile → (5-methyl-1H-indol-4-yl)methanamine

HRID 475298Notes

Reaction equation

HRID 475298 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:11]#[N:12]>N.CO.[Ni]>[CH3:1][C:2]1[C:3]([CH2:11][NH2:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 1

HCID 768467345-methyl-1H-indole-4-carbonitrile

Product 1

HCID 76846757(5-methyl-1H-indol-4-yl)methanamineYield 95.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A mixture of 302 (54 mg, 0.346 mmol) and Raney Ni (100 mg) in 7M ammonia in MeOH (20 mL) was stirred under hydrogen at RT for 3 h. It was filtered through Celite®, and the filtrate was concentrated under reduced pressure to afford 53 mg (95.7%) of (5-methyl-1H-indol-4-yl)methanamine (304) as yellow solid: MS (ESI) m/z=144.3 (M−16).

Workup

  1. filtrationIt was filtered through Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7385944bd4a941fa9eef6221007e81fa
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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