Phenylhydrazine → 2-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde phenylhydrazone

HRID 15703

Reaction equation

HRID 15703 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[C:18]1([NH:24][NH2:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:18]1([NH:24][N:25]=[CH:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[CH:3]2[C:2]([CH3:1])=[C:6]([CH3:7])[C:5]([CH3:8])=[C:4]2[CH3:9])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 1317271152-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde

Product 1

HCID 1317271192-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehyde phenylhydrazoneYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (20.0 mmol) in ethanol (60.0 mL) was added dropwise phenylhydrazine (22.0 mmol) and the mixture was stirred at room temperature for 2-hrs. The solvent was distilled off under reduced pressure and the residue was recrystallized from hexane to give 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde phenylhydrazone (4.8 g, yield 76.3%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-0d645ecf36154d5a942afd04449e7d94
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Linked notes

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