Benzaldehyde → 2-(2-Benzylidenehydrazino)benzoic acid

HRID 552089

Reaction equation

HRID 552089 reaction equation
Cl.[NH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[NH2:3].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O.C(O)C>[CH:13](=[N:3][NH:2][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)

Product 1

HCID 2226872-(2-Benzylidenehydrazino)benzoic acidYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2-hydrazino-benzoic acid mono hydrochloric acid salt (13.66 g, 72.42 mmol) dissolved in water (580 mL) and ethanol (125 mL) was added a solution of benzaldehyde (7.35 mL, 72.42 mmol) in ethanol (20 mL) dropwise at room temperature. The reaction mixture was stirred at room temperature for an additional 3 hours. The resulting solid was collected by filtration and dried in a vacuum oven to provide 12.0 g (69%) of 2-(N′-benzylidene-hydrazino)-benzoic acid as a yellow solid.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. customdried in a vacuum oven

Sources & evidence

ORD record
ord-f6f1e2feb8db4ee79020f74dde7b0dd4
Source dataset
uspto-grants-2011_05
Patent number
US07951800B2

Linked notes

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