Acetic Acid → 4-(4-Chlorophenyl)-1,3-dihydro-indol-2-one

HRID 1839605ノート

反応式

HRID 1839605 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][NH:12]3)=[CH:4][CH:3]=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(=[O:40])C>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][C:11](=[O:40])[NH:12]3)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 21124087PyridiniumtribromideHCID 225617474-(4-Chloro-phenyl)-1H-indole

生成物 1

HCID 225619894-(4-Chlorophenyl)-1,3-dihydro-indol-2-one収率 94%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 86587657t-BuOH ethanol aceticacid溶媒

反応条件

温度
27 °C

実験手順

To the suspension of 4-(4-chloro-phenyl)-1H-indole (1.52 g, 6.68 mmol) in t-BuOH-ethanol-acetic acid (3:2:1) (81 mL) was added pyridinium tribromide (90% purity from Aldrich, 7.12 g, 20.0 mmol)) portionwise. The mixture was stirred at 27° C. for 3 hours, and then to the mixture was added acetic acid (30 mL). Zinc dust was added to the reaction mixture portionwise until the color changed from deep red to light yellow, and the reaction mixture was stirred at room temperature for one hour. The unreacted zinc dust was filtered off and washed with ethanol. The filtrate was concentrated, and the syrupy residue was suspended in water (500 mL) for 0.5 hour. The solid product was precipitated out, filtered, and washed repeatedly with water to remove the zinc salt and pyridine salt. After high vacuum dry, a pure product (1.54 g, 94%) was obtained.

後処理

  1. stirringwas stirred at room temperature for one hour
  2. filtrationThe unreacted zinc dust was filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. waitthe syrupy residue was suspended in water (500 mL) for 0.5 hour
  6. customThe solid product was precipitated out
  7. filtrationfiltered
  8. washwashed repeatedly with water
  9. customto remove the zinc salt and pyridine salt
  10. customAfter high vacuum dry

出典と根拠

ORDレコード
ord-db13ae8ec8e74ef195ffb20f270bd421
出典データセット
uspto-grants-2004_01
特許番号
US06677368B2

反応ノート

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