p-Nitroacetophenone → 3-(4-Nitrophenyl)-1H-pyrazole

HRID 1251466Notes

Reaction equation

HRID 1251466 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=O.COC(OC)[N:16]([CH3:18])C.[NH2:21]N>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([C:2]2[NH:21][N:16]=[CH:18][CH:1]=2)=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 7487p-NitroacetophenoneHCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 27370713-(4-Nitrophenyl)-1H-pyrazoleYield 58.8%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

4-Nitroacetophenone(15 g) and N,N-dimethylformamide dimethylacetal(54 g) were refluxed for 1 hour. The reaction mixture was cooled, then crystals precipitate were filtered. To a solution of the crystals obtained (13.5 g) in ethanol (150 ml) was added hydrazine (4.52 g) and p-toluene sulfonic acid monohydrate (0.15 g) and the mixture was refluxed for 1 hours. The solvent was evaporated to dryness and the residue was crystallized from ether to obtain thr title compound (10.1 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationcrystals precipitate were filtered
  3. customTo a solution of the crystals obtained (13.5 g) in ethanol (150 ml)
  4. temperaturethe mixture was refluxed for 1 hours
  5. customThe solvent was evaporated to dryness
  6. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-743f2d07680d45fe878525b9a98c2a9b
Source dataset
uspto-grants-2002_01
Patent number
US06342516B1

Reaction notes

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