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

HRID 354165Notes

Reaction equation

HRID 354165 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:14][CH2:15][O:16][CH3:17])[N:5]=[C:6]([C:11]([NH2:13])=[O:12])[C:7]=1[N+:8]([O-])=O)[CH3:2]>[Pd].C(O)C>[NH2:8][C:7]1[C:6]([C:11]([NH2:13])=[O:12])=[N:5][N:4]([CH2:14][CH2:15][O:16][CH3:17])[C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 112187175-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

Product 1

HCID 112643124-amino-5-ethyl-1-(2-methoxyethyl)-1H-Pyrazole-3-carboxamideYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (100 mg) was added to a stirred slurry of 3-ethyl-2-(2-methoxyethyl)-4-nitro-pyrazole-5-carboxamide (5 g, 20.77 mmol) in ethanol (100 mL) and the mixture stirred in a pressure vessel under a hydrogen atmosphere (344.7 kPa (50 psi)) at room temperature for 6 h. The mixture was filtered and concentrated. Recrystallisation from hot ethyl acetate gave the product as white crystals (3.5 g). The mother liquor was concentrated to give a further 1.5 g of product as a grey powder.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customRecrystallisation from hot ethyl acetate

Sources & evidence

ORD record
ord-3ef1a7dde81643968328fe800d633c49
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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