Hydrochloric Acid → Acemetacin

HRID 542586

Reaktionsgleichung

Reaktionsgleichung von HRID 542586
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]([O:22][CH2:23][C:24]([O:26]CC=C)=[O:25])=[O:21])=[C:9]2[CH3:30])=[O:7])=[CH:4][CH:3]=1.N1CCCCC1.Cl>O1CCCC1>[CH3:30][C:9]1[N:8]([C:6]([C:5]2[CH:31]=[CH:32][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:7])[C:16]2[CH:15]=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=2[C:10]=1[CH2:19][C:20]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 13654465Allyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetate

Produkt 1

HCID 1981Acemetacin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.003 mole of tetrakis-triphenylphosphine-palladium-(O) is added to 0.03 mole of acemetacin allyl ester in 50 ml of tetrahydrofuran, under nitrogen. 0.3 mole of piperidine is added dropwise at 20°-25° C., with stirring, and stirring is then continued for 2 hours at room temperature (check by thin layer chromatography). 200 ml of half-concentrated hydrochloric acid are added dropwise with cooling, the phases are separated off, the aqueous phase is extracted twice with methylene chloride and the combined organic phases are evaporated in vacuo. The residue is recrystallised from toluene.

Aufarbeitung

  1. stirringstirring
  2. temperaturewith cooling
  3. customthe phases are separated off
  4. extractionthe aqueous phase is extracted twice with methylene chloride
  5. customthe combined organic phases are evaporated in vacuo
  6. customThe residue is recrystallised from toluene

Quellen und Nachweise

ORD-Eintrag
ord-f58d4d42e84347c99776474a7ff89b38
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04658039

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