1-(4-Nitrobenzyl)-1H-pyrazole → 4-(1H-pyrazol-1-ylmethyl)aniline

HRID 1508882Notes

Reaction equation

HRID 1508882 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]1

Participants

4

Reactant 1

HCID 9736631-(4-Nitrobenzyl)-1H-pyrazole

Product 1

HCID 27644124-(1H-pyrazol-1-ylmethyl)anilineYield 66.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

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]+.

Workup

  1. filtrationAfter this time, the mixture was filtered through celite
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-bea9b23ebb814e4c8be8f448d21f0f39
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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