1-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide → 4-amino-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazole-5-carboxamide

HRID 1896198Notes

Reaction equation

HRID 1896198 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]([C:11]([NH2:13])=[O:12])=[C:9]([N+:14]([O-])=O)[C:8]([CH2:17][CH3:18])=[N:7]1)[CH3:2].[H][H]>[Pt].C(OC(C)C)(=O)C>[NH2:14][C:9]1[C:8]([CH2:17][CH3:18])=[N:7][N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[C:10]=1[C:11]([NH2:13])=[O:12]

Participants

5

Reactant 2

HCID 577445561-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 577445394-amino-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 7915Isopropyl AcetateSolvent

Procedure

1-(2-ethoxyethyl)-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide from step 1 (15.0 g, 58 mmol), 5% Platinum-on-carbon (0.75 g), and isopropyl acetate (150 mL) were combined and the mixture was stirred under 80 psi of hydrogen for about 50 hours. The mixture was then filtered through celite, the celite was rinsed with acetonitrile, and the filtrate was concentrated. The material eventually crystallized to give 13.7 g as a hydrate of the title compound.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washthe celite was rinsed with acetonitrile
  3. concentrationthe filtrate was concentrated
  4. customThe material eventually crystallized

Sources & evidence

ORD record
ord-fe48cc5037154e5db3225d1bb8c24ee2
Source dataset
uspto-grants-2013_08
Patent number
US08518956B2

Reaction notes

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