1-(4-Nitrobenzyl)-1H-pyrazole → 4-(1H-pyrazol-1-ylmethyl)aniline
Reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pt]>[N:9]1([CH2:8][C:7]2[CH:14]=[CH:15][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=[N:10]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1-(4-nitrobenzyl)-1H-pyrazole (0.375 g, 1.85 mmol) in ethyl acetate (15 mL) was treated with Pt/C (0.018 g, 0.09 mmol) and the mixture stirred at rt for 16 h under a hydrogen atmosphere. After this time, the mixture was filtered through celite, washed with ethyl acetate, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.213 g, 57%) as a yellow solid. MW=173.21. 1H NMR (CDCl3, 300 MHz) δ 7.58-7.47 (m, 1H), 7.32 (d, J=2.1 Hz, 1H), 7.09-7.01 (m, 2H), 6.68-6.59 (m, 2H), 6.24 (t, J=2.1 Hz, 1H), 5.19 (s, 2H), 3.69 (s, 2H); APCI MS m/z 174 [M+H]+.