tert-butyl 4-nitro-1H-pyrazole-1-carboxylate → tert-butyl 4-amino-1H-pyrazole-1-carboxylate

HRID 577287Notes

Reaction equation

HRID 577287 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:8]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:8]=1

Participants

4

Reactant 1

HCID 66765764tert-butyl 4-nitro-1H-pyrazole-1-carboxylate

Product 1

HCID 59587648tert-butyl 4-amino-1H-pyrazole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-butyl 4-nitro-1H-pyrazole-1-carboxylate was stirred with palladium on carbon (10%, 170 mg) in ethanol (20 mL) under an atmosphere of hydrogen at 20° C. for 18 h. The palladium was removed by filtration and the solvent was removed in vacuo to give tert-butyl 4-amino-1H-pyrazole-1-carboxylate (1.48 g). 1H NMR (d6-DMSO) δ 7.35 (d, 1H), 7.33 (d, 1H), 4.40 (s, 2H), 1.54 (s, 9H).

Workup

  1. customThe palladium was removed by filtration
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-04f9edca0c134f42a0c0f9eff08eb84a
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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