Hydrazine hydrate (1:1) → 4-(2-Methoxyphenyl)-1H-pyrazole

HRID 1581807Notes

Reaction equation

HRID 1581807 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[CH:5]=O.O.[NH2:17]N>C(O)C>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:3]=[N:2][NH:17][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 865899133-Dimethylamino-2-(2-methoxyphenyl)propenal

Product 1

HCID 227234704-(2-Methoxyphenyl)-1H-pyrazoleYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-dimethylamino-2-(2-methoxyphenyl)propenal (4.68 g, 22.8 mmol) and hydrazine hydrate (6.7 ml) in ethanol (100 ml) is heated at reflux for 30 minutes. The solvent is removed in vacuo and the residue is chromatographed (silica gel, dichloromethane/ethanol 95:5) to give 2.69 g of 4-(2-methoxyphenyl)pyrazole (68%).

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe solvent is removed in vacuo
  3. customthe residue is chromatographed (silica gel, dichloromethane/ethanol 95:5)

Sources & evidence

ORD record
ord-5eed3c7b1660419eb4b7d03afb07a3e3
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

Loading…