Water → 4-Phenylindolin-2-one

HRID 983004

反応式

HRID 983004 の反応式
[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

参加物

8

反応物 3

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

生成物 1

HCID 130486014-Phenylindolin-2-one収率 67%

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒2 回HCID 702Ethanol溶媒HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-019143f702134c938a561e745cea973f
出典データセット
uspto-grants-2005_03
特許番号
US06861418B2

関連ノート

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