Salicylic acid, hydrazide → Benzoic acid, 2-hydroxy-, 2-(1-oxo-3-phenyl-2-propenyl)hydrazide

HRID 972176Notes

Reaction equation

HRID 972176 reaction equation
[C:1]([NH:10][NH2:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:12](Cl)(=[O:21])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[C:12]([NH:11][NH:10][C:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])(=[O:21])[CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 13637Salicylic acid, hydrazideHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 116536Benzoic acid, 2-hydroxy-, 2-(1-oxo-3-phenyl-2-propenyl)hydrazideYield 32.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To 50 ml of N-dimethylacetamide were added 5.0 g of salicyloylhydrazine and 5.5 g of cinnamoyl chloride, and the mixture was stirred at 20° C for 9 hours. The reaction mixture was then poured into 2 liters of water, and the produced precipitate was collected by filtration and washed with water. The so obtained product was then recrystallized twice from acetic acid and dried under reduced pressure to yield 3 g of N-cinnamoyl-N'-salicyloylhydrazine as white crystals, m.p. 271° C. Analysis: Calculated for C16H14N2O3 ; C, 68.09%, H, 4.96%; N, 9.93%, Found: C, 68.08%; H, 4.81%; N, 9.08%.

Workup

  1. filtrationthe produced precipitate was collected by filtration
  2. washwashed with water
  3. customThe so obtained product
  4. customwas then recrystallized twice from acetic acid
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-abd8ee92318f4601a37c4894afcec706
Source dataset
uspto-grants-1977_10
Patent number
US04052362

Reaction notes

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