Ethyl benzoate → Benzoylhydrazine

HRID 880381Notes

Reaction equation

HRID 880381 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:13][NH2:14]>C(O)C>[C:1]([NH:13][NH2:14])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7165Ethyl benzoateHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 11955Benzoylhydrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100 ml 3-neck flask were added 40 ml of ethanol and 6 g of ethyl benzoate, to which 12.5 g of 85% hydrazine hydrate was added slowly and dropwise with stirring. After the addition was completed, the mixture was heated under reflux for 8 hours and then cooled to room temperature. The solvent was distilled under reduced pressure and water was added. The solid was precipitated. The mixture was allowed to stand for 30 min until the solid was fully precipitated, which was filtrated and washed with water. Recrystallization with anhydrous ethanol gave benzoyl hydrazine.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 8 hours
  4. distillationThe solvent was distilled under reduced pressure and water
  5. additionwas added
  6. customThe solid was precipitated
  7. customwas fully precipitated
  8. filtrationwhich was filtrated
  9. washwashed with water
  10. customRecrystallization with anhydrous ethanol

Sources & evidence

ORD record
ord-984d46e1535643f5b54c2d59fc5bf5e5
Source dataset
uspto-grants-2015_03
Patent number
US08993575B2

Reaction notes

Loading…