Hydrochloric Acid → 1-(2-Chloro-6-fluorophenyl)-5-methylindolin-2-one

HRID 1280860

Reaktionsgleichung

Reaktionsgleichung von HRID 1280860
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]([C:17](=[O:20])[CH2:18]Cl)[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.O>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:10]2[C:15](=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH2:18][C:17]1=[O:20]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 46729202-chloro-N-(2-chloro-6-fluorophenyl)-N-(4-methylphenyl)acetamideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 112428411-(2-Chloro-6-fluorophenyl)-5-methylindolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 72391,2-DichlorobenzeneLösungsmittel

Versuchsvorschrift

A mixture of 100 g (0.32 mol) of N-(2′-chloro-6′-fluorophenyl)-N-chloroacetyl-4-methylaniline and 110 g (0.82 mol) of aluminum chloride in 400 ml of 1 ,2-dichlorobenzene is stirred vigorously and heated to 140° for 7.5 hours. The reaction is cooled to room temperature and added to a mixture of 100 ml of 12N HCl and 700 ml of water (cooled to 0-5° in a dry ice/acetone bath). The mixture is extracted twice with 400 ml of methylene chloride and the combined organic layers are washed with 600 ml of 3N HCl. The organic layer is stirred with 66 g of magnesium sulfate and 33 g of charcoal (DARCO G-60). The solids are filtered through a pad of Celite and the solvents are evaporated under reduced pressure to give a tan solid which is recrystallized from ethanol to give N-(2′-chloro-6′-fluorophenyl)-5-methyloxindole, m.p. 137-140°.

Aufarbeitung

  1. temperatureheated to 140° for 7.5 hours
  2. extractionThe mixture is extracted twice with 400 ml of methylene chloride
  3. washthe combined organic layers are washed with 600 ml of 3N HCl
  4. stirringThe organic layer is stirred with 66 g of magnesium sulfate and 33 g of charcoal (DARCO G-60)
  5. filtrationThe solids are filtered through a pad of Celite
  6. customthe solvents are evaporated under reduced pressure
  7. customto give a tan solid which
  8. customis recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c733e02b26aa42079a8f06fb670c43c4
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451858B2

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