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Potassium Hydroxide → HCID 178524696, Verbindung

HRID 505878
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 505878
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][C:12]1[O:17][CH2:18][O:19][C:11]=1[CH:10]=2)=[O:5])C.[OH-].[K+]>C(O)C>[OH:16][C:15]1[C:14]2[C:9](=[CH:10][C:11]3[O:19][CH2:18][O:17][C:12]=3[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 84257Ethyl 8-hydroxy-(1,3)dioxolo(4,5-g)quinoline-7-carboxylate

Produkt 1

HCID 178524696HCID 178524696, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Hydroxy-6,7-methylenedioxy-3-quinolinecarboxylic acid ethyl ester (45.0 g, 0.172 mol) was added to a solution of KOH (16.8 g, 0.258 mol) in ethanol (500 mL) and the mixture was heated to reflux with stirring for 20 hours. The reaction flask was then cooled and ethanol was evaporated under reduced pressure. Then 800 mL of water were added with stirring to fully dissolve the potassium salt, and the solution was filtered to remove any impurities. Concentrated HCl was added to bring the mixture to pH 1, and the free acid was filtered off and dried under vacuum, to give 33.9 g as a beige solid, in 84%; mp >300° C. (lit.221 mp >290° C.); 1H NMR (DMSO-d6) δ 6.27 (s, 2H), 7.30 (s, 1H), 7.55 (s, 1H), 8.72 (s, 1H); 13C NMR (DMSO-d6) δ 98.5, 101.8, 103.8, 107.9, 120.8, 137.9, 143.5, 148.1, 153.7, 167.4, 177.4.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction flask was then cooled
  4. customethanol was evaporated under reduced pressure
  5. additionThen 800 mL of water were added
  6. stirringwith stirring
  7. dissolutionto fully dissolve the potassium salt
  8. filtrationthe solution was filtered
  9. customto remove any impurities
  10. additionConcentrated HCl was added
  11. filtrationthe free acid was filtered off
  12. customdried under vacuum
  13. customto give 33.9 g as a beige solid

Quellen und Nachweise

ORD-Eintrag
ord-7f3e4c815930414bb06361a1ce835eac
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781587B2

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