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 467731Notes

Reaction equation

HRID 467731 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-db43834ca35e43fa9989b438790a7927
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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