Hydrochloric Acid → 1-Phenyloxindole

HRID 751329

Reaktionsgleichung

Reaktionsgleichung von HRID 751329
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=O)[C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O.NN.Cl>C(O)CO.O>[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 128841-PhenylisatinHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)

Produkt 1

HCID 3147871-PhenyloxindoleAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of commercially available 1-phenyl-1H-indole-2,3-dione (10.10 g, 45.7 mmol) in ethylene glycol (125 mL) is added powdered potassium hydroxide (7.4 g, 112 mmol), hydrazine hydrate (16.35 mL) and water (4 mL). The reaction is heated to 160° C. for 1.5 hr after which it is cooled to room temperature, made acidic with conc. hydrochloric acid, diluted with water and the resulting solids are collected by filtration. The solid is washed with water, dissolved in dichloromethane, dried and the solvent removed to give the 1-phenyl-1H-indol-2-one (8.6 g, 90% yield) as a solid.

Aufarbeitung

  1. temperatureis cooled to room temperature
  2. filtrationthe resulting solids are collected by filtration
  3. washThe solid is washed with water
  4. dissolutiondissolved in dichloromethane
  5. customdried
  6. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-3db108bdf9ab4cf4acff58245c1627ce
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405300B2

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