1-(Cyclopropylmethyl)-4-nitro-1H-pyrazole → 1-(cyclopropylmethyl)-1H-pyrazol-4-amine

HRID 1478053Notes

Reaction equation

HRID 1478053 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[N:6]2)[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][N:5]2[CH:9]=[C:8]([NH2:10])[CH:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 510000071-(Cyclopropylmethyl)-4-nitro-1H-pyrazole

Product 1

HCID 435603721-(cyclopropylmethyl)-1H-pyrazol-4-amineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(cyclopropylmethyl)-4-nitro-1H-pyrazole (8.37 g, 50.1 mmol) in methanol (150 mL) was added 10% Pd/C (840.0 mg, 0.7893 mmol). The suspension was stirred at room temperature under a H2 atmosphere for 2 h. Filtered and the filter cake was washed with MeOH (50 mL×3). The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/100 to 1/50) to give the title compound as purple oil (5.5 g, 80%).

Workup

  1. filtrationFiltered
  2. washthe filter cake was washed with MeOH (50 mL×3)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/100 to 1/50)

Sources & evidence

ORD record
ord-79e0edf7ef7f4f68b4f729c53ba7ccd2
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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