tert-butyl-3-nitro-5-cyclopropyl-1H-pyrazole-1-carboxylate → tert-butyl 3-amino-5-cyclopropyl-1H-pyrazole-1-carboxylate

HRID 1935333Notes

Reaction equation

HRID 1935333 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([CH:13]2[CH2:15][CH2:14]2)=[CH:11][C:10]([N+:16]([O-])=O)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:12]([CH:13]2[CH2:14][CH2:15]2)=[CH:11][C:10]([NH2:16])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11265267tert-butyl-3-nitro-5-cyclopropyl-1H-pyrazole-1-carboxylate

Product 1

HCID 11218347tert-butyl 3-amino-5-cyclopropyl-1H-pyrazole-1-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.2 g (4.74 mmol) of tert-butyl-3-nitro-5-cyclopropyl-1H-pyrazole-1-carboxylate were dissolved in 20 ml of ethanol and hydrogenated in presence of 200 mg of palladium on charcoal 10% at 50 psi and room temperature to give, after filtration on celite and evaporation of the solvent, 0.96 g (95% yield) of the title compound.

Workup

  1. customto give
  2. filtrationafter filtration

Sources & evidence

ORD record
ord-f5fa94ed91264816b207650519461718
Source dataset
uspto-grants-2002_05
Patent number
US06387900B1

Reaction notes

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