Hydrochloric Acid → 5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

HRID 366564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366564
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:15][CH2:16][C:17](Cl)=[O:18].Cl>ClC(Cl)C.C(OCC)(=O)C>[Cl:15][CH2:16][C:17]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2)=[O:18]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-oneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

2-Oxindole (6.7 g) was added to a stirred suspension of 23 g of aluminum chloride in 30 mL of dichloroethane in an ice bath. Chloroacetyl chloride (11.3 g) was slowly added and hydrogen chloride gas was evolved. After ten minutes of stirring, the reaction was warmed at 40 to 50° C. for 1.5 hours. Thin layer chromatography (ethyl acetate, silica gel) showed no remaining starting material. The mixture was cooled to room temperature and poured into ice water. The precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 10.3 g (98%) of 5-chloroacetyl-2-oxindole as an off-white solid.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dec44caaeee243b2bc7f5e3de4486466
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130238

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