HCID 178511141, compound → 1-(2,5-difluorophenyl)-1H-pyrazol-5-amine

HRID 1466578Notes

Reaction equation

HRID 1466578 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1/[N:9]=[N:10]/[CH2:11][CH2:12][C:13]#[N:14]>[OH-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N:9]1[C:13]([NH2:14])=[CH:12][CH:11]=[N:10]1

Participants

3

Reactant 1

HCID 178511141HCID 178511141, compound

Product 1

HCID 668510491-(2,5-difluorophenyl)-1H-pyrazol-5-amineYield 88.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of (E)-3-((2,5-difluorophenyl)diazenyl)propanenitrile (710 mg) and 20 mL of 1N NaOH was heated to reflux with stirring for 30 min. The reaction mixture was cooled to ambient temperature and extracted with ether. The ether phase was washed with water, brine, dried over sodium sulfate and filtered through a plug of silica gel. Concentration under vacuum gave 630 mg (88%) of 1-(2,5-difluorophenyl)-1H-pyrazol-5-amine. LCMS (ESI) m+H=196.0; 1H NMR (400 MHz, CDCl3) δ 7.54-7.43 (m, 1H), 7.35-7.00 (m, 3H), 5.63 (d, 1H), 3.96-3.71 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. extractionextracted with ether
  4. washThe ether phase was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through a plug of silica gel
  7. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-2a7eaf996e2f4a7cb3b01871c1fff527
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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