Hydrazine → 1,2-Dihydro-6-nitro-3H-indazol-3-one

HRID 1176022Notes

Reaction equation

HRID 1176022 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1F.[NH2:15][NH2:16]>C(O)C>[N+:10]([C:7]1[CH:6]=[C:5]2[C:4]([C:3](=[O:2])[NH:15][NH:16]2)=[CH:9][CH:8]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 3013872Methyl 2-fluoro-4-nitrobenzoate

Product 1

HCID 32644791,2-Dihydro-6-nitro-3H-indazol-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude material, 2-fluoro-4-nitro-benzoic acid methyl ester, from above was treated with hydrazine (1.6 mL, 51 mmol) in ethanol under reflux for 14 hrs. After removal of solvent by evaporation, the residue was washed with water. The precipitate product was filtered and dried on the vacuum pump to give the title compound which was used without further purification (4.0 g, 85% for two steps). MS (ES+): m/e=180.1 (M+H), 178.0 (M-H); LC/Method A 1.83 min.

Workup

  1. temperatureunder reflux for 14 hrs
  2. customAfter removal of solvent
  3. customby evaporation
  4. washthe residue was washed with water
  5. filtrationThe precipitate product was filtered
  6. customdried on the vacuum pump

Sources & evidence

ORD record
ord-eeb45d2046d84206b9d86b8d6fdf86ab
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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