Benzaldehyde → 5-Amino-3-methyl-1-phenylpyrazole

HRID 1586141Notes

Reaction equation

HRID 1586141 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].O.[NH2:6][NH2:7].C(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:16](O)C>>[NH2:4][C:1]1[N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]=[C:3]([CH3:16])[CH:2]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 7855AcrylonitrileHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 708015-Amino-3-methyl-1-phenylpyrazole

Procedure

A mixture of acrylonitrile (15.3 g, 0.289 mol) and ethanol (75 ml) is stirred in an ice-bath and then hydrazine hydrate (15 ml, 0.3 mol) is added dropwise and the mixture is warmed to room temperature and stirred for 2 hours. Benzaldehyde (30.6 ml, 0.3 mol) is then added, and the reaction mixture is stirred at room temperature for about 2 days. The react on mixture is concentrated in vacuo and the residue is added to a solution of sodium butoxide in butanol [prepared from sodium metal (6.9 g) and butanol (300 ml)]. The reaction mixture is refluxed overnight, and then the solvent is concentrated in vacuo to afford 19.4 g of crude 5-amino-1-phenyl methylpyrazole.

Workup

  1. stirringstirred for 2 hours
  2. stirringthe reaction mixture is stirred at room temperature for about 2 days
  3. customThe react on mixture
  4. concentrationis concentrated in vacuo
  5. additionthe residue is added to a solution of sodium butoxide in butanol [prepared from sodium metal (6.9 g) and butanol (300 ml)]
  6. temperatureThe reaction mixture is refluxed overnight
  7. concentrationthe solvent is concentrated in vacuo

Sources & evidence

ORD record
ord-01be8681d59d4567bf9cbe282a4ad0c1
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

Loading…