1-(3-methoxy-4-nitro-1H-pyrazol-1-yl)propan-2-ol → 1-(3-methoxy-4-amino-1H-pyrazol-1-yl)propan-2-ol
Reaction equation
[CH3:1][O:2][C:3]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]([CH2:11][CH:12]([OH:14])[CH3:13])[N:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[C:7]([NH2:8])=[CH:6][N:5]([CH2:11][CH:12]([OH:14])[CH3:13])[N:4]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A nitrogen-flushed round bottom flask was charged with 1-(3-methoxy-4-nitro-1H-pyrazol-1-yl)propan-2-ol (345 mg, 1.72 mmol, 1.00 eq), 10% Pd/C (200 mg) and methanol (20 mL). The reaction mixture was sparged with hydrogen for 10 min then stirred vigorously under hydrogen atmosphere for 14 hr. The reaction mixture was then sparged with nitrogen, filtered through Celite®, and concentrated to give the title compound as an oil that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.92 (s, 1H) 4.70 (d, J=4.9 Hz, 1H) 3.89-3.77 (m, 1H) 3.74 (s, 3H) 3.73-3.55 (m, 2H) 0.97 (d, J=6.2 Hz, 3H). m/z (APCI+) for C7H14N3O2 172.3 (M+H)+.