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

HRID 467719Notes

Reaction equation

HRID 467719 reaction equation
[OH:1][C:2]([CH3:17])([CH3:16])[CH2:3][NH:4][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]([NH:4][CH2:3][C:2]([OH:1])([CH3:16])[CH3:17])=[O:6])=[N:8][N:9]([CH3:15])[CH:10]=1

Participants

4

Reactant 1

HCID 70115746N-(2-Hydroxy-2-methylpropyl)-1-methyl-4-nitro-1H-pyrazole-3-carboxamide

Product 1

HCID 653557454-Amino-N-(2-hydroxy-2-methylpropyl)-1-methyl-1H-pyrazole-3-carboxamideYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(2-hydroxy-2-methylpropyl)-1-methyl-4-nitro-1H-pyrazole-3-carboxamide (391 mg, 1.61 mmol) in ethanol was added under an argon atmosphere Pd/C 10% (40 mg, 0.04 mmol) at ambient temperature. The mixture was stirred at that temperature under a hydrogen atmosphere for 16 hours. The catalyst was filtered off and washed with ethanol. The filtrate was concentrated in vacuo to give the title compound as waxy solid (340 mg, 99% yield) which was used without any further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bd70741b7c8042e88648159ac52f0d46
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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