Hydrochloric Acid → 1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-

HRID 128547

Reaktionsgleichung

Reaktionsgleichung von HRID 128547
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15]C(OC)=O)=[CH:10][C:9]=1[N:20]1[C:24](=[O:25])[C:23]2[CH2:26][CH2:27][CH2:28][CH2:29][C:22]=2[C:21]1=[O:30].Cl>CO>[F:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([OH:15])=[CH:10][C:9]=1[N:20]1[C:24](=[O:25])[C:23]2[CH2:26][CH2:27][CH2:28][CH2:29][C:22]=2[C:21]1=[O:30]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 19374481N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

Produkt 1

HCID 1586511H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-Ausbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Potassium carbonate (4.6 g, 33.3 mmol) was added to a solution of N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (11.8 g, 33.4 mmol) obtained as described above in methanol (100 ml), followed by stirring for 5 hours under refluxing. After completion of the reaction, the mixture was poured into 1N hydrochloric acid (200 ml), and the mixture was extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with water, dried, and the solvent was distilled off under reduced pressure to obtain a crude product (9.4 g). The product was recrystallized from ether/hexane to obtain N-(2-fluoro-4-chloro-5-hydroxypheyl) 3,4,5,6-tetrahydrophthalimide as a white solid (6.7 g 22.7 mmol, 67.8% yield).

Aufarbeitung

  1. customobtained
  2. temperatureunder refluxing
  3. customAfter completion of the reaction
  4. extractionthe mixture was extracted with ethyl acetate (100 ml×3 times)
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain a crude product (9.4 g)
  9. customThe product was recrystallized from ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-bede846e461842c3949928f1d2de4866
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464811

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