Hydrochloric Acid → 5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one

HRID 640827

反応式

HRID 640827 の反応式
[Al+3].[Cl-].[Cl-].[Cl-].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6].[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C:18]1=[O:26].Cl>O.CN(C=O)C>[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[NH:17][C:18](=[O:26])[CH2:19]3)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 687007145-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one収率 96%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

AlCl3 (20.0 g, 150 mmol) was placed in a dry 200 mL round bottom flask and DMF (3.30 mL) was added dropwise at 0° C. During the addition of DMF care was taken to ensure that the reaction was allowed to vent to the outside as this addition caused an exotherm to occur. Additionally as the DMF was added a white suspension formed. This suspension was allowed to stir for 30 min at room temperature, after which 4-nitrobenzoyl chloride (2.984 g, 16 mmol) was added. The mixture was warmed to 50° C. and stirred for 15 min at that temperature. The 50° C. mixture then was treated with oxindole (2.051 g, 15 mmol). The resulting reaction mixture was heated to 90° C. and allowed to stir for 5 hours during which the reaction mixture turned from a yellowish suspension to a thick black oil. The reaction was cooled to room temperature. Ice was added directly to the flask followed by water, turning the black oil into a pale yellow/white precipitate. Concentrated HCl(aq) (3 mL) was added to the reaction and the contents were stirred at room temperature for 15 min. The precipitate was collected via vacuum filtration. The crude solid was purified by washing with sat. NaHCO3(aq) providing 5-(4-Nitro-benzoyl)-1,3-dihydro-indol-2-one as a gray solid (4.05 g, 14.4 mmol, 95%).

後処理

  1. additionoutside as this addition
  2. customformed
  3. temperatureThe mixture was warmed to 50° C.
  4. stirringstirred for 15 min at that temperature
  5. customThe resulting reaction mixture
  6. temperaturewas heated to 90° C.
  7. stirringto stir for 5 hours during which the reaction mixture
  8. temperatureThe reaction was cooled to room temperature
  9. additionIce was added directly to the flask
  10. stirringthe contents were stirred at room temperature for 15 min
  11. filtrationThe precipitate was collected via vacuum filtration
  12. customThe crude solid was purified
  13. washby washing with sat. NaHCO3(aq)

出典と根拠

ORDレコード
ord-3eff361f05ac4d189a169f420da34441
出典データセット
uspto-grants-2010_04
特許番号
US07692005B2

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