N,N,1-trimethyl-4-nitropyrazole-3-carboxamide → 4-Amino-N,N,1-trimethyl-1H-pyrazole-3-carboxamide

HRID 2368231Notes

Reaction equation

HRID 2368231 reaction equation
[CH3:1][N:2]([CH3:14])[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][N:2]([CH3:14])[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 67076071N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

Product 1

HCID 653550564-Amino-N,N,1-trimethyl-1H-pyrazole-3-carboxamideYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid dimethylamide (100 mg, 0.5 mmol) in ethanol (4 ml) was flushed with argon and treated with Pd/C5% (40 mg, 0.02 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 an off-white solid material (83 mg, 98%) 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-a53c952c409a4df9aca132455590e2c5
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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