1-Isopropyl-4-nitro-1H-pyrazole → 1-(Propan-2-yl)-1H-pyrazol-4-amine

HRID 1930385Notes

Reaction equation

HRID 1930385 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[N:5]1)([CH3:3])[CH3:2]>CCO.[Pd]>[CH:1]([N:4]1[CH:8]=[C:7]([NH2:9])[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 134698241-Isopropyl-4-nitro-1H-pyrazole

Product 1

HCID 134698261-(Propan-2-yl)-1H-pyrazol-4-amineYield 75.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-isopropyl-4-nitro-1 H-pyrazole (3 g, 19 mmol) in EtOH (30 mL) was stirred under a hydrogen atmosphere for 2 h in the presence of 10% Pd/C (300 mg). The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 1-isopropyl-1 H-pyrazol-4-ylamine (1.8 g, 75.0% yield). 1H NMR (400 MHz, DMSO-d6): δ 6.99 (s, 1 H), 6.84 (s, 1 H), 4.23 (m, 1 H), 3.70 (s, 2 H), 1.28 (d, J=6.8 Hz, 6 H); MS (ESI) m/z: 126.2[M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-443df12da81446a3933fd4d5c58c039e
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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