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

HRID 567796Notes

Reaction equation

HRID 567796 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:6]([CH2:8][C:9]#[N:10])=O.O.[NH2:17][NH2:18]>C(O)C>[NH2:10][C:9]1[CH:8]=[C:6]([C:5]2[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:18][N:17]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70223633-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile

Product 1

HCID 43585515-(3,4-Dimethoxyphenyl)-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dimethoxybenzoylacetonitrile (3.6 g) was dissolved in ethanol (20 ml) to which was subsequently added hydrazine monohydrate (0.87 ml) under cooling with ice. The mixture was heated under reflux for 7 hours and allowed to cool. Then, the solvent was distilled away under a reduced pressure. The resultant residue was recrystallized from ethyl acetate to obtain the title compound (2.92 g) as colorless crystals (melting point: 124-125° C.).

Workup

  1. temperatureunder cooling with ice
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 7 hours
  4. temperatureto cool
  5. distillationThen, the solvent was distilled away under a reduced pressure
  6. customThe resultant residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c50b4fd68b804c958ed07c3d58d8d39b
Source dataset
uspto-grants-2001_01
Patent number
US06180653B2

Reaction notes

Loading…