tert-Butyl 3-methyl-4-nitro-1H-pyrazole-1-carboxylate → tert-Butyl 4-amino-3-methyl-1H-pyrazole-1-carboxylate

HRID 1045959Notes

Reaction equation

HRID 1045959 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-])=O)=[CH:5][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[N:3]=1>CO.[Pd]>[NH2:7][C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH:5]=1

Participants

4

Reactant 1

HCID 60027346tert-Butyl 3-methyl-4-nitro-1H-pyrazole-1-carboxylate

Product 1

HCID 60027404tert-Butyl 4-amino-3-methyl-1H-pyrazole-1-carboxylateYield 56.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 3-methyl-4-nitropyrazole-1-carboxylate (815 mg) was dissolved in MeOH (20 ml) and hydrogenated at room temperature for 40 hours with 10% Pd/C (0.2 g, 50% wet). The catalyst was filtered off and the solvent removed in vacuo. Column chromatography on silica (4 g), eluting with 1:1 EtOAc-heptane (500 ml) gave tert-butyl 4-amino-3-methylpyrazole-1-carboxylate (400 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed in vacuo
  3. washColumn chromatography on silica (4 g), eluting with 1:1 EtOAc-heptane (500 ml)

Sources & evidence

ORD record
ord-9af916266417465bb3a2c821e3a5036d
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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