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

HRID 467634Notes

Reaction equation

HRID 467634 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-46409b41216d43798b2ac3987db62749
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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