Hydrazine hydrate (1:1) → 1,2-Dihydro-6-nitro-3H-indazol-3-one

HRID 56612Notes

Reaction equation

HRID 56612 reaction equation
F[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].O.[NH2:16][NH2:17]>C(O)C.C(OCC)(=O)C>[N+:12]([C:10]1[CH:11]=[C:2]2[C:3]([C:4](=[O:5])[NH:16][NH:17]2)=[CH:8][CH:9]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 3013872Methyl 2-fluoro-4-nitrobenzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In two portions of equal size, a total of 2.00 g (10.0 mmol) of methyl 2-fluoro-4-nitrobenzoate and 2.51 g (50.2 mmol) of hydrazine monohydrate in 36 ml of ethanol were heated in a microwave reactor at 120° C. for 2 h. The combined reaction solutions were diluted with ethyl acetate and washed with water. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. Yield: 1.66 g (purity 95%, 88% of theory)

Workup

  1. customThe combined reaction solutions
  2. washwashed with water
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf55c5f94a744d7c8134953f9a135937
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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