Isopropanol → 9-Ethyl-3-carbazolecarbaldehyde n-2,3-epoxypropyl-n-phenylhydrazone

HRID 1611888Notes

Reaction equation

HRID 1611888 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]=[CH:15][CH:16]=2)[CH3:10].[CH:26]([OH:29])([CH3:28])[CH3:27]>>[O:29]1[CH2:28][CH:26]1[CH2:27][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[N:8]=[CH:24][C:20]1[CH:21]=[CH:22][C:23]2[N:11]([CH2:9][CH3:10])[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 7516PhenylhydrazineHCID 820559-ethyl-9H-carbazole-3-carbaldehyde

Product 1

HCID 731765569-Ethyl-3-carbazolecarbaldehyde n-2,3-epoxypropyl-n-phenylhydrazone

Procedure

Phenylhydrazine (0.1 mole, commercially available from Aldrich, Milwaukee, Wis.) and 9-ethyl-3-carbazolecarboxaldehyde (0.1 mole, available from Aldrich Chemical, Milwaukee, Wis.) were dissolved in 100 ml of isopropanol 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 9-ethyl-3-carbazolecarbaldehyde phenylhydrazone crystals formed upon standing were filtered off and washed with isopropanol and dried in vacuum oven at 50° C. for 6 hours.

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-05ccefa600034a769f1f54a7aca60e6d
Source dataset
uspto-grants-2006_01
Patent number
US06991882B2

Reaction notes

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