Ammonia → 5-(Aminomethyl)-1H-indazole
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.N.[H][H]>C1COCC1.CO.[Ni]>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a suspension of 1H-indazole-5-carbonitrile (0.235 g, 1.64 mmol) in THF (6 mL) was added 2 mL of 2 N ammonia in methanol and the flask was charged with 0.05 g Raney® 2800 nickel. A hydrogen balloon was attached to the flask and the system was purged 3 times with hydrogen. After stirring vigorously overnight the reaction mixture was diluted with methanol and filtered through a pad of celite. The solvent was evaporated in vacuo to provide 1-(1H-indazole-5-yl)methanamine.
Workup
- customthe system was purged 3 times with hydrogen
- additionwas diluted with methanol
- filtrationfiltered through a pad of celite
- customThe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-1219f384a4d142bdb185821b5e1b19a3
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08436016B2
Reaction notes
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