5-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole → 5-(Azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine
Reaction equation
[N:1]1([CH2:5][C:6]2[N:10]([CH3:11])[N:9]=[C:8]([N+:12]([O-])=O)[CH:7]=2)[CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[N:1]1([CH2:5][C:6]2[N:10]([CH3:11])[N:9]=[C:8]([NH2:12])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-(azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole (349 mg, 1.78 mmol) in ethanol (20 mL) was treated with palladium on carbon (10%, 50 mg). The resulting mixture was stirred under a hydrogen (1 atm) for 48 h. The reaction mixture was filtered through a celite pad, and the pad washed with ethanol. The filtrate was concentrated in vacuo to give 5-(azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine (292 mg, 99%) as a light yellow oil. 1H NMR (300 MHz, DMSO-d6) 8 ppm 1.93 (quin, J=6.89 Hz, 2 H) 3.06 (t, J=6.99 Hz, 4 H) 3.34 (s, 2 H) 3.46 (s, 3 H) 4.36 (s, 2 H) 5.25 (s, 4 H).