Pyrazole → 1-(4-Nitrophenyl)-1H-pyrazole

HRID 1709692Notes

Reaction equation

HRID 1709692 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[Na].F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

7

Reactant 5

HCID 1048Pyrazole2×HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5360545Sodium

Product 1

HCID 6050591-(4-Nitrophenyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Pyrazole (2.0 g, 29 mmol) in tetrahydrofuran (THF) is added dropwise to a suspension of 50% sodium hydride (1.4 g) in THF at RT, followed by stirring at RT for 2 hours. The resulting sodium salt of pyrazole is added to 4-fluoronitrobenzene (4.15 g) in THF at 0°, after which the mixture is heated under reflux for 15 hours. The reaction mixture is poured into saturated aq. ammonium chloride and extracted with ethyl acetate. The combined organic layers are washed with water and with brine and dried to give 1-(4-nitrophenyl)pyrazole.

Workup

  1. temperatureafter which the mixture is heated
  2. temperatureunder reflux for 15 hours
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers are washed with water and with brine
  5. customdried

Sources & evidence

ORD record
ord-560537fe8d72493b88b4ee78a306bba1
Source dataset
uspto-grants-1990_08
Patent number
US04950678

Reaction notes

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