HCID 17862346, compound → HCID 17862348, compound

HRID 644845Notes

Reaction equation

HRID 644845 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=2[C:17]([F:20])([F:19])[F:18])[CH:3]=1.[H][H]>C(O)C.[C].[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][C:4]2[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=2)=[C:9]([C:17]([F:20])([F:19])[F:18])[CH:10]=1

Participants

5

Reactant 2

HCID 17862346HCID 17862346, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 17862348HCID 17862348, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-methyl-3-(4-nitro-2-trifluoromethylphenyloxy)pyrazole (5.3 g, 18.5 mmol) in ethanol (200 ml) was placed in an autoclave, and 10% palladium carbon (2.0 g) was added. An atmosphere in the autoclave was fully replaced with hydrogen gas, and hydrogen gas was filled up to 5 kg/cm2. Then, the reaction solution was stirred at room temperature for 4 hours. After completion of the reaction, the catalyst was separated by filtration using Celite, and the solvent was distilled off from the filtrate under reduced pressure, to give a white solid of 3-(4-amino-2-trifluoromethylphenyloxy)-5-methylpyrazole (3.6 g, yield: 76.1%). mp: 143-145° C.; 1H-NMR (DMSO-d6, DMSO, ppm): δ 2.17 (s, 3H), 5.33 (br s, 2H), 5.44 (s, 1H), 6.78 (dd, J=2.6 and 8.8 Hz, 1H), 6.88 (d, J=2.6 Hz, 1H), 6.95 (d, J=8.8 Hz, 1H), 11.80-11.95 (br s, 1H).

Workup

  1. additionwas added
  2. additionwas filled up to 5 kg/cm2
  3. customAfter completion of the reaction
  4. customthe catalyst was separated by filtration
  5. distillationthe solvent was distilled off from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-7c4adcab037e4c75af8364e4725076a5
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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