HCID 59812796, compound → 1H-Pyrazole-5-carboxylic acid, 4-amino-1-methyl-, ethyl ester

HRID 2368365Notes

Reaction equation

HRID 2368365 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:14])[N:8]=[CH:9][C:10]=1[N+:11]([O-])=O)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:14])[N:8]=[CH:9][C:10]=1[NH2:11])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 59812796HCID 59812796, compound

Product 1

HCID 601364511H-Pyrazole-5-carboxylic acid, 4-amino-1-methyl-, ethyl esterYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid ethyl ester (1.97 g, 9.89 mmol; prepared from 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid according to WO 2009/026241) in EtOH (20 ml) under argon atmosphere was added 10% Pd/C (200 mg). The black suspension was stirred at r.t. under a hydrogen atmosphere for 20 h. The catalyst was filtered off and washed with EtOH. The product was obtained upon evaporation as light brown oil (1.63 g, 97%) and used without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with EtOH

Sources & evidence

ORD record
ord-43a991dc9b1443fa83d953721b0f9c3f
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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