2-ethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester → 5-amino-2-ethyl-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1256779Notes

Reaction equation

HRID 1256779 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:13][CH3:14])[N:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)=[O:4]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:13][CH3:14])[N:7]=[C:8]([NH2:10])[CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 576192792-ethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 576194165-amino-2-ethyl-2H-pyrazole-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 2-ethyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester (526, 1.30 g, 6.53 mmol) in methanol (60.0 mL) was added 20% Pd(OH)2/C (0.1 g). The reaction was stirred under an atmosphere of hydrogen overnight. The reaction was filtered and concentrated to give a light yellow solid (527, 1.0 g, 90.6%).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customto give a light yellow solid (527, 1.0 g, 90.6%)

Sources & evidence

ORD record
ord-2a5ab8a12f444f6f89e93b1693b7c46b
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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