Hydrochloric Acid → 6-Chloro-5-fluoroindolin-2-one

HRID 248429

Reaktionsgleichung

Reaktionsgleichung von HRID 248429
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11]([O:13]C)=O.O.Cl>C(Cl)Cl.C(O)(=O)C>[F:9][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[Cl:8])[NH:1][C:11](=[O:13])[CH2:10]2

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid3×HCID 962WaterHCID 10900080Methyl (2-amino-4-chloro-5-fluorophenyl)acetate2×

Produkt 1

HCID 97940836-Chloro-5-fluoroindolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel3×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Compound (III) is obtained by cyclizing (II) with an acid as shown in step [b] of Scheme 1. Compound (II) is dissolved in a mixture of an acid and a cosolvent, preferably the acid is glacial acetic acid in which instance the preferred cosolvent is water or the acid is hydrochloric acid in which instance the preferred cosolvent is methylene chloride. With acetic acid the ratio of the acid and cosolvent mixture ranges from 2:1 to pure acetic acid respectively, the preferred ratio being 6:1. With HCl, much less acid is required, preferably 1:4 3N HCl to CH2Cl2. Once compound (II) is dissolved, the reaction mixture is stirred at ambient temperature for from 6 to 7 hours to produce 5-fluoro-6-chlorooxindole (III). Compound (III) is readily purified by recrystallization from ethyl acetate to yield an off-white solid.

Quellen und Nachweise

ORD-Eintrag
ord-e96b6c2225c34fcbb498b079655072ef
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05210212

Verknüpfte Notizen

Wird geladen…