Pyrrolidine → (3Z)-3-(((4Z,6Z,8E)-azulen-1-yl)methylene)-5-phenylindolin-2-one

HRID 2236124Notes

Reaction equation

HRID 2236124 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH:27]=O)[C:26]2[C:20]([CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:19][CH:18]=1.N1CCCC1>C(O)C>[C:17]1(/[CH:27]=[C:10]2\[C:11](=[O:16])[NH:12][C:13]3[C:9]\2=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:15][CH:14]=3)=[CH:18][CH:19]=[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=[C:26]12

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 117448701-Azulene carboxyaldehydeHCID 133019785-Phenyloxindole

Product 1

HCID 59301667(3Z)-3-(((4Z,6Z,8E)-azulen-1-yl)methylene)-5-phenylindolin-2-oneYield 22.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.4389 g 5-phenyloxindole (0.0021 mole) and 0.323 g azulene aldehyde (0.0021 mole) were dissolved in 30 mL dried ethanol. 1.5 mL pyrrolidine (1M) was then added and uniformly stirred at reflux temperature for two hours. After removal of dried ethanol, the results were extracted by dichloromethane and citric acid aqueous solution. The organic layer was collected, dried with anhydrous magnesium sulfate, filtered, concentrated under vacuum, and separated by silica gel column chromatography to give Z-form Compound 034 (0.1621 g).

Workup

  1. temperatureat reflux temperature for two hours
  2. customAfter removal of dried ethanol
  3. extractionthe results were extracted by dichloromethane and citric acid aqueous solution
  4. customThe organic layer was collected
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customseparated by silica gel column chromatography

Sources & evidence

ORD record
ord-d6dd7afe5b17411d803f1f4e5aa4aa26
Source dataset
uspto-grants-2010_05
Patent number
US07714146B2

Reaction notes

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