2-[1,2,4]triazol-1-yl-nicotinonitrile → 1-[2-(1H-1,2,4-Triazol-1-yl)pyridin-3-yl]methanamine
Reaction equation
[N:1]1([C:6]2[N:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]#[N:9])[CH:5]=[N:4][CH:3]=[N:2]1>O.N.CO.[Ni]>[N:1]1([C:6]2[C:7]([CH2:8][NH2:9])=[CH:10][CH:11]=[CH:12][N:13]=2)[CH:5]=[N:4][CH:3]=[N:2]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A catalytic amount of Raney 2800 nickel in water (Aldrich; withdrawn as a wet slurry with the tip of a spatula) was added under air to a translucent slurry of 2-[1,2,4]triazol-1-yl-nicotinonitrile (1.053 g, 6.16 mmol), as prepared in the previous step, in 2 M NH3/MeOH (50 mL). The flask was then sealed with a septum, the air was removed from the system, and the flask was flushed with H2 gas under balloon pressure. The reaction was stirred at rt under H2 for 11 h (TLC showed no starting material remained), and the bulk of the Raney nickel was then removed with a magnet. The translucent white reaction mixture was then diluted with DCM (50 mL), filtered, and the translucent filtrate was concentrated under vacuum to provide the title compound as a beige crystalline solid (988 mg, 92%).
Workup
- customwithdrawn as a wet slurry with the tip of a spatula)
- customThe flask was then sealed with a septum
- customthe air was removed from the system
- customthe flask was flushed with H2 gas under balloon pressure
- customwas then removed with a magnet
- additionThe translucent white reaction mixture was then diluted with DCM (50 mL)
- filtrationfiltered
- concentrationthe translucent filtrate was concentrated under vacuum
Sources & evidence
- ORD record
- ord-0a1a887a954a4216be2b7e5eee342312
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829584B2
Reaction notes
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