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

HRID 2236124노트

반응식

HRID 2236124 반응식
[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

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 117448701-Azulene carboxyaldehydeHCID 133019785-Phenyloxindole

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d6dd7afe5b17411d803f1f4e5aa4aa26
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714146B2

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