N-[4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-N-propyl-3-nitrobenzamide → N-[4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-N-propyl-3-aminobenzamide

HRID 848957Notes

Reaction equation

HRID 848957 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([N:16]([CH2:28][CH2:29][CH3:30])[C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)[CH2:3]1>C(O)(=O)C.[Pd]>[O:1]=[C:2]1[N:6]([C:7]2[C:8]([Cl:15])=[CH:9][C:10]([Cl:14])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([N:16]([CH2:28][CH2:29][CH3:30])[C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 19369062N-[4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-N-propyl-3-nitrobenzamide

Product 1

HCID 19369057N-[4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-N-propyl-3-aminobenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N-[4,5-Dihydro-5-oxo-1-(2,4,6-trichlorophenyl)-1H-pyrazol-3-yl]-N-propyl-3-nitrobenzamide (33.0 g, 68.3 mmol) was dissolved in glacial acetic acid (300 ml) and 10% palladium on charcoal (3.2 g) was added. The mixture was hydrogenated under pressure (30 atms) for 4 hrs, then the catalyst was removed by filtration through Kieselguhr. The solvent was removed by evaporation and the product was dried under vacuum to give a white glass, 32.5 g, ca 100%. The product was used in the next stage without purification.

Workup

  1. customthe catalyst was removed by filtration through Kieselguhr
  2. customThe solvent was removed by evaporation
  3. customthe product was dried under vacuum
  4. customto give a white glass, 32.5 g, ca 100%
  5. customThe product was used in the next stage without purification

Sources & evidence

ORD record
ord-09dfc17b50244317b1a521a514adfb5d
Source dataset
uspto-grants-2000_01
Patent number
US06010837

Reaction notes

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