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

HRID 2400520Notes

Reaction equation

HRID 2400520 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[N:5]1)([CH3:3])[CH3:2]>C(O)C.[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 115.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of impure 1-isopropyl-4-nitro-1H-pyrazole (1) (1.23 g), from above, in ethanol (50 mL) was treated with 10% palladium on carbon (400 mg, 50% water by weight) and shaken under a hydrogen atmosphere (35 psi) at room temperature for 1 h. After this time, the reaction was filtered through diatomaceous earth and the filtrate concentrated under reduced pressure to afford 1-isopropyl-1H-pyrazole-4-amine (2) (1.15 g) as an impure off-white solid, which was used without further purification: 1H NMR (300 MHz, DMSO-d6) δ 7.02 (s, 1H), 6.87 (s, 1H), 4.26 (m, 1H), 3.72 (bs, 2H), 1.42 (d, J=6.6 Hz, 6H).

Workup

  1. filtrationAfter this time, the reaction was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-217ecb8e62214fba9378ab593549e0e3
Source dataset
uspto-grants-2014_08
Patent number
US08796270B2

Reaction notes

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