Salicylaldehyde → N-[(2-Hydroxyphenyl)methylidene]benzenecarbohydrazonic acid

HRID 355168Notes

Reaction equation

HRID 355168 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:11](=O)[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[OH:14]>O>[CH:11](=[N:10][NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[OH:14]

Participants

4

Reactant 2

HCID 6998SalicylaldehydeHCID 11955Benzoylhydrazine

Product 1

HCID 160674N-[(2-Hydroxyphenyl)methylidene]benzenecarbohydrazonic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 13.6 g (0.10 mole) of benzhydrazide and 50 ml of water, and the vessel contents were agitated as 13.4 g (0.11 mole) of salicylaldehyde was added. Heat was evolved and the mixture was stirred at room temperature for an additional hour, then warmed briefly on a steam bath. The precipitate which had formed was filtered off, washed with water and ether, and dried under vacuum. It was then placed in 300 ml of ethanol for several hours and the remaining solid, crystalline in appearance, was filtered off and dried under vacuum. The filtrate was then diluted with water and cooled, forming additional precipitate which was then filtered off and dried. Both precipitates were combined to yield 19.0 g (79% of theoretical yield) of salicylidene benzhydrazide, with a melting point range of 172°-174° C.

Workup

  1. additionwas added
  2. temperatureHeat
  3. temperaturewarmed briefly on a steam bath
  4. customThe precipitate which had formed
  5. filtrationwas filtered off
  6. washwashed with water and ether
  7. customdried under vacuum
  8. waitIt was then placed in 300 ml of ethanol for several hours
  9. filtrationthe remaining solid, crystalline in appearance, was filtered off
  10. customdried under vacuum
  11. additionThe filtrate was then diluted with water
  12. temperaturecooled
  13. customforming additional precipitate which
  14. filtrationwas then filtered off
  15. customdried

Sources & evidence

ORD record
ord-b9e1640efdbb4c9caa8cee3d7f30c2dc
Source dataset
uspto-grants-1983_03
Patent number
US04378239

Reaction notes

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