Methanol → 3-p-Fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

HRID 647997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 647997
[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH2:15][CH:16]([C:17]([O:19]C(C)C)=[O:18])[C:11]3=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.CO.C(=O)([O-])[O-].[K+].[K+]>O>[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:11]3=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 20484013Isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate

Produkt 1

HCID 134870783-p-Fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 180 mg. of isopropyl 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylate in 5 ml. of methanol is treated with a solution of 200 mg. of potassium carbonate in 1.5 ml. of water. The reaction mixture is refluxed under a nitrogen atmosphere for 24 hours, cooled, and evaporated to dryness. The residue is taken up in water and the resultant mixture extracted with ethyl acetate to remove the neutral impurities. The aqueous phase is made acidic with concentrated hydrochloric acid and the product is extracted with ethyl acetate. The extract is washed with sodium chloride, dried over sodium sulfate and evaporated to dryness under reduced pressure. Crystallization of the residue from acetone hexane affords 3-p-fluorobenzoyl-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid (XIa, R=H, L=p-F, n=1), m.p. 164° C.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed under a nitrogen atmosphere for 24 hours
  2. temperaturecooled
  3. customevaporated to dryness
  4. extractionthe resultant mixture extracted with ethyl acetate
  5. customto remove the neutral impurities
  6. extractionthe product is extracted with ethyl acetate
  7. washThe extract is washed with sodium chloride
  8. dry with materialdried over sodium sulfate
  9. customevaporated to dryness under reduced pressure
  10. customCrystallization of the residue from acetone hexane

Quellen und Nachweise

ORD-Eintrag
ord-fce93d69eb7f4b72b117cec32385afe9
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04410534

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