4-chloro-3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole → 4-chloro-3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

HRID 1265358Notes

Reaction equation

HRID 1265358 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:17]([F:18])=[CH:16][C:15]([Cl:19])=[C:14]([O:20][CH3:21])[C:13]=2[N+:22]([O-])=O)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]>C1(C)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[C:3]([C:12]2[C:17]([F:18])=[CH:16][C:15]([Cl:19])=[C:14]([O:20][CH3:21])[C:13]=2[NH2:22])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:9])([F:8])[F:10]

Participants

4

Reactant 1

HCID 186156314-chloro-3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

Product 1

HCID 186156594-chloro-3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazoleYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

4-Chloro-3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole (0.48 g, 1.24 mmol) was dissolved in toluene (8 ml) and 0.05 g of 10% palladium on carbon was added. The solution was vigorously stirred under hydrogen atmosphere for 4 hr at ambient temperature and the catalyst was removed by filtration. Removal of the solvent afforded a residue which was chromatographed on silica gel. Elution of the column with hexanemethylene chloride (3:7) furnished the title compound (0.38 g).

Workup

  1. customthe catalyst was removed by filtration
  2. customRemoval of the solvent
  3. customafforded a residue which
  4. customwas chromatographed on silica gel
  5. washElution of the column with hexanemethylene chloride (3:7)

Sources & evidence

ORD record
ord-f91ef3c6478f4c569bf8b7f8099bf7c1
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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