3-(Heptafluoropropyl)-5-methyl-4-nitro-1H-pyrazole → 3-Heptafluoropropyl-5-methyl-1H-pyrazol-4-ylamine

HRID 270800Notes

Reaction equation

HRID 270800 reaction equation
[F:1][C:2]([F:19])([C:15]([F:18])([F:17])[F:16])[C:3]([F:14])([F:13])[C:4]1[C:8]([N+:9]([O-])=O)=[C:7]([CH3:12])[NH:6][N:5]=1>C(O)(=O)C.[Zn]>[F:19][C:2]([F:1])([C:15]([F:17])([F:18])[F:16])[C:3]([F:13])([F:14])[C:4]1[C:8]([NH2:9])=[C:7]([CH3:12])[NH:6][N:5]=1

Participants

4

Reactant 1

HCID 27749443-(Heptafluoropropyl)-5-methyl-4-nitro-1H-pyrazole

Product 1

HCID 210711353-Heptafluoropropyl-5-methyl-1H-pyrazol-4-ylamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a suspension of zinc dust (1.5 g) in glacial acetic acid (10 mL) was added drop-wise, a solution of 3-Heptafluoropropyl-5-methyl-4-nitro-1H-pyrazole (0.295 g, 1.0 mmol) in glacial acetic acid (5 mL). The reaction mixture was then allowed to stir at room temperature for 14 h. The zinc salts were then removed by filtration and the residue washed with ethyl acetate. The combined organic extract was concentrated in vacuum, re-dissolved in CHCl3, washed with NaHCO3, water and brine. Finally the organic layer was dried with Na2SO4 and solvent evaporated to give the title compound as white solid.

Workup

  1. additionwas added drop-wise
  2. customThe zinc salts were then removed by filtration
  3. washthe residue washed with ethyl acetate
  4. extractionThe combined organic extract
  5. concentrationwas concentrated in vacuum
  6. dissolutionre-dissolved in CHCl3
  7. washwashed with NaHCO3, water and brine
  8. dry with materialFinally the organic layer was dried with Na2SO4 and solvent
  9. customevaporated

Sources & evidence

ORD record
ord-ff935f5470e2488ab1ecae973eadb675
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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