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

HRID 1372020Notes

Reaction equation

HRID 1372020 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 vaccum, 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 vaccum
  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-95652f6f54bc41bfbfaf4ba1f240c3dc
Source dataset
uspto-grants-2007_01
Patent number
US07157464B2

Reaction notes

Loading…