Acetic Acid → Acemetacin

HRID 1659165

Reaktionsgleichung

Reaktionsgleichung von HRID 1659165
C(O[CH:5]([O:12][C:13](=[O:36])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]([C:26](=[O:34])[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:16]=1[CH3:35])C1C=CC=CC=1)(=O)C.[C:37]([OH:40])(=[O:39])C>[C].[Pd]>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:26]([N:17]2[C:18]3[C:23](=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:15]([CH2:14][C:13]([O:12][CH2:5][C:37]([OH:40])=[O:39])=[O:36])=[C:16]2[CH3:35])=[O:34])=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 70621351[1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-benzyl acetate

Produkt 1

HCID 1981Acemetacin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418390HCID 178418390, VerbindungKatalysator

Versuchsvorschrift

25.4 g (0.050 mol) of [1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-benzyl acetate were dissolved in 400 ml of glacial acetic acid and hydrogenated on 2.0 g of palladium carbon at room temperature. After the absorption of hydrogen had finished (1 hour), the catalyst was filtered off, the filtrate was concentrated by evaporation under vacuum and the compound was caused to crystallise by adding petroleum ether. The compound melted at 149.5°-150.5°C (determined on the micro-Kofler bench); the yield was 19.4 g which corresponds to 93% of the theoretical yield.

Aufarbeitung

  1. customAfter the absorption of hydrogen
  2. custom(1 hour)
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated by evaporation under vacuum
  5. customto crystallise
  6. additionby adding petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-ab3ee72757984b029418cf8de4248ca2
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03966956

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