Ammonia → (3-Methylimidazo[1,2-a]pyridin-6-yl)methanamine

HRID 1890582Notes

Reaction equation

HRID 1890582 reaction equation
[CH3:1][C:2]1[N:6]2[CH:7]=[C:8]([C:11]#[N:12])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.N>CO.[Ni]>[CH3:1][C:2]1[N:6]2[CH:7]=[C:8]([CH2:11][NH2:12])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 592142593-Methylimidazo[1,2-A]pyridine-6-carbonitrile

Product 1

HCID 67305671(3-Methylimidazo[1,2-a]pyridin-6-yl)methanamineYield 97.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-methylimidazo[1,2-a]pyridine-6-carbonitrile (6-2) (200 mg, 1.27 mmol) in methanol (30 mL) were added Raney nickel (slurry in water, 100 mg) and 1N ammonia. The reaction mixture was stirred under H2 for 2 h, then filtered and concentrated to afford the title compound (200 mg). MS (m/z): 162 (M+H)+

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5de6c37af71f4cdd9249954e15059d42
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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