tert-butyl 5-nitro-1H-pyrazol-3-ylcarbamate → tert-butyl N-(5-amino-1H-pyrazol-3-yl)carbamate
Reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[NH:8][N:7]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH:5]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To 5.88 g (25.77 mmol) of tert-butyl 5-nitro-1H-pyrazol-3-ylcarbamate diluted in 145 ml of methanol, are added under inert atmosphere 600 mg of palladium on charcoal (10%), then the reaction mixture is stirred under hydrogen atmosphere for 24 h. The solution is filtered on Celite and rinsed with ethyl acetate. The filtrate is concentrated to yield 4.93 g of tert-butyl 5-amino-1H-pyrazol-3-ylcarbamate in the form of a grey solid.