N-(2-Hydroxy-2-methylpropyl)-N,1-dimethyl-4-nitro-1H-pyrazole-3-carboxamide → 4-Amino-N-(2-hydroxy-2-methylpropyl)-N,1-dimethyl-1H-pyrazole-3-carboxamide

HRID 2368328Notes

Reaction equation

HRID 2368328 reaction equation
[OH:1][C:2]([CH3:18])([CH3:17])[CH2:3][N:4]([CH3:16])[C:5]([C:7]1[C:11]([N+:12]([O-])=O)=[CH:10][N:9]([CH3:15])[N:8]=1)=[O:6]>C(O)C.[Pd]>[NH2:12][C:11]1[C:7]([C:5]([N:4]([CH2:3][C:2]([OH:1])([CH3:17])[CH3:18])[CH3:16])=[O:6])=[N:8][N:9]([CH3:15])[CH:10]=1

Participants

4

Reactant 1

HCID 70115754N-(2-Hydroxy-2-methylpropyl)-N,1-dimethyl-4-nitro-1H-pyrazole-3-carboxamide

Product 1

HCID 793845594-Amino-N-(2-hydroxy-2-methylpropyl)-N,1-dimethyl-1H-pyrazole-3-carboxamideYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(2-hydroxy-2-methylpropyl)-N,1-dimethyl-4-nitro-1H-pyrazole-3-carboxamide (1.2 g, 4.7 mmol) in ethanol (30 ml) was flushed with argon and treated with palladium on carbon 10% (120 mg, 1.13 mmol). The reaction mixture was evacuated and flushed with hydrogen and stirred at ambient temperature for 16 h. The reaction mixture was filtered, washed with ethanol and concentrated in vacuo to yield the product as dark red oil (1.0 g, 80%) which was used without any further purification.

Workup

  1. customThe reaction mixture was evacuated
  2. customflushed with hydrogen
  3. filtrationThe reaction mixture was filtered
  4. washwashed with ethanol
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62c4421232534559a7ce13b07889a064
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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