Hydrazine hydrate (1:1) → 5-(3,4-Dichlorophenyl)-1H-pyrazol-3-amine

HRID 1276296Notes

Reaction equation

HRID 1276296 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:5]([CH2:7][C:8]#[N:9])=O.O.[NH2:15][NH2:16]>C(O)C>[NH2:9][C:8]1[CH:7]=[C:5]([C:4]2[CH:10]=[CH:11][C:12]([Cl:13])=[C:2]([Cl:1])[CH:3]=2)[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27580633-(3,4-Dichlorophenyl)-3-oxopropanenitrile

Product 1

HCID 14891585-(3,4-Dichlorophenyl)-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dichlorobenzoylacetonitrile (3.0 g) was dissolved in ethanol (15 ml) to which was subsequently added hydrazine monohydrate (0.67 ml) while cooling with ice. The mixture was heatedunder reflux for 5 hours and allowed to cool. Then, the solvent was distilled away under a reduced pressure. The resulting residue was recrystallized from ethyl acetate-hexane to obtain the title compound (1.72 g) as colorless crystals (melting point: 169-170° C.).

Workup

  1. temperaturewhile cooling with ice
  2. temperaturereflux for 5 hours
  3. temperatureto cool
  4. distillationThen, the solvent was distilled away under a reduced pressure
  5. customThe resulting residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-333c8339502a4ebe84936fe7bbd2d169
Source dataset
uspto-grants-2000_12
Patent number
US06166038

Reaction notes

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