N,1-dimethyl-4-nitropyrazole-3-carboxamide → 4-amino-N,1-dimethyl-1H-pyrazole-3-carboxamide

HRID 2368233Notes

Reaction equation

HRID 2368233 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:9]([N+:10]([O-])=O)=[CH:8][N:7]([CH3:13])[N:6]=1)=[O:4]>C(O)C.[Pd]>[CH3:1][NH:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][N:7]([CH3:13])[N:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 1256475N,1-dimethyl-4-nitropyrazole-3-carboxamide

Product 1

HCID 70175484-amino-N,1-dimethyl-1H-pyrazole-3-carboxamideYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid methylamide (100 mg, 0.5 mmol) in ethanol (4 ml) was flushed with argon and treated with Pd/C 10% (40 mg, 0.04 mmol). The reaction vessel was evacuated and flushed with hydrogen three times and the reaction was stirred at ambient temperature overnight. The reaction mixture was filtrated and the solvent was evaporated to yield a brown viscous oil (76 mg, 91%) which was used without further purification.

Workup

  1. customThe reaction vessel was evacuated
  2. customflushed with hydrogen three times
  3. filtrationThe reaction mixture was filtrated
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bd5412ab6a3e4924984ad235d771698b
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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