2-Hydrazinoethanol → 2-(3-Amino-1H-pyrazol-1-yl)ethan-1-ol

HRID 2291329Notes

Reaction equation

HRID 2291329 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][NH2:5].C(=O)([O-])[O-].[K+].[K+].Cl[C:13](=[CH2:16])[C:14]#[N:15]>O>[NH2:15][C:14]1[CH:13]=[CH:16][N:4]([CH2:3][CH2:2][OH:1])[N:5]=1

Participants

5

Reactant 3

HCID 80172-HydrazinoethanolHCID 11430Potassium CarbonateHCID 701982-Chloroacrylonitrile

Product 1

HCID 212798532-(3-Amino-1H-pyrazol-1-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Hydroxyethylhydrazine (7.6 g.) was added slowly to a solution of potassium carbonate (13.8 g.) in water (40 ml.). The mixture was cooled to 0°, then 2-chloroacrylonitrile (8.75 g.) was added slowly with vigorous stirring. Stirring was continued for a further 17 hours and the mixture was then continuously extracted with EtOAc for 20 hours. On evaporation of the solvent, 3-amino-1-(2-hydroxyethyl)pyrazole was obtained (7.7 g.; 60%), b.p. 170/0.5 mm.

Workup

  1. temperatureThe mixture was cooled to 0°
  2. extractionthe mixture was then continuously extracted with EtOAc for 20 hours
  3. customOn evaporation of the solvent

Sources & evidence

ORD record
ord-e28cdb01f4594714898e089b1da349d3
Source dataset
uspto-grants-1989_01
Patent number
US04795755

Reaction notes

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