Pyrrolidine → Z-6-chloro-3-(3,3-dimethyl-butylidene)-1,3-dihydro-indol-2-one

HRID 1727947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727947
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:12][C:13]([CH3:18])([CH3:17])[CH2:14][CH:15]=O.N1CCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:15]/[CH2:14][C:13]([CH3:18])([CH3:17])[CH3:12])/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 763353,3-DimethylbutanalHCID 7363446-Chloro-1,3-dihydroindol-2-one

Produkt 1

HCID 86615083Z-6-chloro-3-(3,3-dimethyl-butylidene)-1,3-dihydro-indol-2-oneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the mixture of 6-chlorooxindole (0.26 g, 1.49 mmol) (Crescent) and 3,3-dimethyl-butyraldehyde (0.21 g, 2.09 mmol) (Aldrich) in methanol (20 mL) was added pyrrolidine (0.15 g, 2.09 mmol) (Aldrich) dropwise. The mixture was then heated at 100° C. for 1 h. The mixture was concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, concentrated, and dried in vacuo to give the crude E/Z-6-chloro-3-(3,3-dimethyl-butylidene)-1,3-dihydro-indol-2-one as a white solid (Yield 0.37 g, 100%).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6f1ccc43c2244600ba1f8144cbf92c43
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495007B2

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