Water → 4-Phenylindolin-2-one

HRID 983004

반응식

HRID 983004 반응식
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[CH:10][NH:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[OH2:37]>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:37])[NH:11]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

8

반응물 3

HCID 962WaterHCID 158062984-Phenyl-1H-indoleHCID 21124087Pyridiniumtribromide

생성물 1

HCID 130486014-Phenylindolin-2-one수율 67%

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 176Acetic Acid용매2회HCID 702Ethanol용매HCID 6386tert-Butanol용매

실험 절차

To the suspension of 4-phenyl-1H-indole (1.1 g, 5.7 mmol) in 2-methyl-2-propanol (33 mL), ethanol (22 mL) and acetic acid (11 mL) was added pyridinium tribromide (90% purity from Aldrich, 6.1 g, 17.1 mmol) portionwise over 10 minutes. The mixture was stirred at room temperature for 2 hours, and then to the mixture was added acetic acid (50 mL). After stirring at room temperature for one hour, water (0.5 mL) and zinc (3.7 g, 57 mmol) were added to the reaction mixture and stirring was continued for another hour. The unreacted zinc dust was filtered off and washed with methanol. The filtrate was concentrated and the syrupy residue was suspended in water (100 mL) for overnight. The solid product was filtered, washed repeatedly with water to remove the zinc salt and pyridine salt. After high vacuum dry, 800 mg (67%) of 4-phenyl-1,3-dihydro-indol-2-one as a light yellow solid was obtained.

후처리

  1. stirringAfter stirring at room temperature for one hour
  2. stirringstirring
  3. waitwas continued for another hour
  4. filtrationThe unreacted zinc dust was filtered off
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated
  7. waitthe syrupy residue was suspended in water (100 mL) for overnight
  8. filtrationThe solid product was filtered
  9. washwashed repeatedly with water
  10. customto remove the zinc salt and pyridine salt
  11. customAfter high vacuum dry

출처 및 근거

ORD 기록
ord-019143f702134c938a561e745cea973f
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06861418B2

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