N-(2-Chloro-3-pyridinyl)-1-methyl-4-nitro-1H-pyrazole-5-carboxamide → 4-amino-N-(2-chloro-3-pyridinyl)-1-methyl-1H-pyrazole-5-carboxamide

HRID 1702438Notes

Reaction equation

HRID 1702438 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1>O1CCOCC1.[Pd]>[NH2:17][C:12]1[CH:13]=[N:14][N:15]([CH3:16])[C:11]=1[C:9]([NH:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)=[O:10]

Participants

4

Reactant 1

HCID 20503812N-(2-Chloro-3-pyridinyl)-1-methyl-4-nitro-1H-pyrazole-5-carboxamide

Product 1

HCID 205038164-amino-N-(2-chloro-3-pyridinyl)-1-methyl-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 62.0 gm (0.22 mol) of N-(2-chloro-3-pyridinyl)-1-methyl-4-nitro-1H-pyrazole-5-carboxamide in 1 liter of dioxane was hydrogenated in the presence of 5 gm of 10% palladium/animal charcoal as catalyst at room temperature and 5 bar until the hydrogen absorption was finished. After removal of the catalyst and the resulting precipitate by filtration, the filtrate was evaporated in vacuo. The remaining distillation residue was recrystallized from methanol.

Workup

  1. custom5 bar until the hydrogen absorption
  2. customAfter removal of the catalyst
  3. filtrationthe resulting precipitate by filtration
  4. customthe filtrate was evaporated in vacuo
  5. distillationThe remaining distillation residue
  6. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-c142b70a43e14fec866689ee3137dbb1
Source dataset
uspto-grants-1983_04
Patent number
US04381303

Reaction notes

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