Hydrazine hydrate (1:1) → 3-Amino-5-nitroindazole

HRID 1823906Notes

Reaction equation

HRID 1823906 reaction equation
[OH2:1].[NH2:2][NH2:3].F[C:5]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=[O:14])=[CH:9][C:6]=1[C:7]#[N:8]>CCO>[N+:13]([C:10]1[CH:9]=[C:6]2[C:5](=[CH:12][CH:11]=1)[NH:3][N:2]=[C:7]2[NH2:8])([O-:14])=[O:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 31366553-Amino-5-nitroindazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (17.5 mL, 362 mmol) was added to a hot (50° C.) solution of 2-fluoro-5-nitrobenzonitrile (30 g, 181 mmol) in EtOH (500 mL). The mixture was heated at reflux for 4 hours then allowed to cool to room temperature, whereupon the product precipitated from solution. The filtrate was concentrated and the residue partitioned between EtOAc and saturated ammonium chloride solution. The organic phase was separated, dried over magnesium sulfate and concentrated to obtain further product. The combined product (32.2 g, quant.) was taken on to the following step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customprecipitated from solution
  4. concentrationThe filtrate was concentrated
  5. customthe residue partitioned between EtOAc and saturated ammonium chloride solution
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto obtain further product
  10. customThe combined product (32.2 g, quant.) was taken on to the following step without further purification

Sources & evidence

ORD record
ord-167c0a4812dc4e25a15bfece85d46da1
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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