Water → HCID 4448611, Verbindung

HRID 1278928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1278928
C(N(CC)CC)C.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[CH:21]=[CH:22][C:23](Cl)=[O:24].O>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:23]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)=[O:24])[CH:26]=[CH:27][CH:28]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 10328IndolineHCID 53411290HCID 53411290, Verbindung

Produkt 1

HCID 4448611HCID 4448611, VerbindungAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Triethylamine (9.2 ml) was added at room temperature to a solution of indoline (20 g) in DCM (200 ml) and the mixture was cooled till 5° C. A solution of m-chlorocinnamoyl chloride (40 g) in DCM (100 ml) was added dropwise and the mixture was stirred at room temperature for 48 hours. Water was added, the organic layer was decanted, washed with water, dried, filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 90/10), yielding 41 g (73%) of 1-[3-(3-chlorophenyl)-1-oxo-2-propenyl]-2,3-dihydro-1H-indole (interm. 37).

Aufarbeitung

  1. customthe organic layer was decanted
  2. washwashed with water
  3. customdried
  4. filtrationfiltered off
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-d46c3ccfc544455e94a79d5fd0e05ddc
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06444812B1

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