HCID 17862451, compound → HCID 17862386, compound

HRID 644911Notes

Reaction equation

HRID 644911 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[N+:22]([O-])=O)=[N:6]1)=[O:4].[H][H]>C(O)C.[C].[Pd]>[CH3:1][NH:2][C:3]([N:5]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:13]=2[NH2:22])=[N:6]1)=[O:4]

Participants

5

Reactant 2

HCID 17862451HCID 17862451, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 17862386HCID 17862386, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of N-methyl-5-methyl-3-(2-nitro-4-trifluoromethylphenyloxy)pyrazole-1-carboxamide (2.1 g, 6.0 mmol) in ethanol (50 ml) was placed in an autoclave, and 10% palladium carbon (0.7 g) was added. An atmosphere in the autoclave was fully replaced with hydrogen gas, and hydrogen gas was charged up to 5 kg/cm2. Then, the reaction solution was stirred at room temperature for 5 hours. After completion of the reaction, the catalyst was removed by filtration using Celite, and the solvent was distilled off from the filtrate under reduced pressure, to give a yellowish solid of N-methyl-3-(2-amino-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxamide (1.6 g, yield: 82.2%). mp: 93-94; 1H-NMR (CDCl3, TMS, ppm): δ 2.59 (d, J=0.7 Hz, 3H), 2.93 (d, J=5.0 Hz, 1H), 3.90-4.15 (br s, 2H), 5.71 (q, J=0.7 Hz, 1H), 6.80-6.95 (m, 1H), 6.97 (dd, J=1.7 and 8.4 Hz, 1H), 7.11 (d, J=8.4 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-fea5a8f39fcd48aba7808bba0274145b
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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