Phenylhydrazine → N-ethyl-3,6-diformylcarbazole bis(N-phenylhydrazone)

HRID 349145

Reaction equation

HRID 349145 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([N:11]1[C:23]2[CH:22]=[CH:21][C:20]([CH:24]=O)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[C:15]([CH:26]=O)[CH:16]=2)[CH3:10]>C1(C)C=CC=CC=1.C1COCC1>[C:1]1([NH:7][N:8]=[CH:24][C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:11]([CH2:9][CH3:10])[C:12]2[CH:13]=[CH:14][C:15]([CH:26]=[N:8][NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:16][C:17]3=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 37166759-ethyl-9H-carbazole-3,6-dicarbaldehyde

Product 1

HCID 69210930N-ethyl-3,6-diformylcarbazole bis(N-phenylhydrazone)

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phenylhydrazine (0.2 mole, commercially available from Aldrich, Milwaukee, Wis.) and N-ethyl-3,6-diformylcarbazole (0.1 mole) were dissolved in 100 ml of a 1:1 v/v mixture of toluene and THF in 250 ml 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The solution was refluxed for 2 hours. Thin layer chromatography indicated the disappearance of the starting materials. At the end of the reaction, the mixture was cooled to room temperature. The N-ethyl-3,6-diformylcarbazole bis(N-phenylhydrazone) crystals formed upon standing were filtered off, washed with isopropanol and dried in a vacuum oven at 50° C. for 6 hours. Without further purification, the product was used for the next step.

Workup

  1. customequipped with a reflux condenser and a mechanical stirrer
  2. temperatureThe solution was refluxed for 2 hours
  3. customAt the end of the reaction

Sources & evidence

ORD record
ord-a579947bca0647aaace9a377a5b0c050
Source dataset
uspto-grants-2007_02
Patent number
US07179574B2

Linked notes

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