HCID 58403540, compound → (3-methyl-1H-indol-4-yl)methanamine

HRID 475268Notes

Reaction equation

HRID 475268 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][CH:3]=1>N.CO.[Ni]>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][NH2:12])[NH:4][CH:3]=1

Participants

5

Reactant 1

HCID 58403540HCID 58403540, compound

Product 1

HCID 83815702(3-methyl-1H-indol-4-yl)methanamineYield 97.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 232 (200 mg, 1.28 mmol) in 7 N NH3 in MeOH (10 mL) was added Raney nickel (20 mg) and the solution was stirred under hydrogen (1 atm.) at RT overnight. The dark mixture was filtered and the filtrate was concentrated under reduced pressure to afford 200 mg (91%) (3-methyl-1H-indol-4-yl)methanamine (234) as white solid: MS (ESI) m/z=144.3 [M−16]+.

Workup

  1. filtrationThe dark mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f8a1291dc47249ef90b568a104b0f5a9
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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