Acetylisatin → 2-Hydroxyquinoline-4-carboxylic acid

HRID 2225335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2225335
[OH-:1].[Na+].[C:3]([N:6]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9](=O)[C:7]1=[O:8])(=[O:5])[CH3:4]>O>[C:7]([C:9]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:6][C:3](=[O:5])[CH:4]=1)([OH:1])=[O:8]

Komponenten

4

Edukt 2

HCID 11321AcetylisatinHCID 14798Sodium Hydroxide

Produkt 1

HCID 850762-Hydroxyquinoline-4-carboxylic acidAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution containing 30 g of sodium hydroxide in 1.5 liter of water was added 58 g of the above-mentioned N-acetylisatin and the mixture was refluxed for 1 hour. Then the reaction mixture was cooled a certain extent, then activated carbon was added and further refluxed for 30 minutes. The activated carbon was removed from the reaction mixture by filtration while the mixture being hot, and the mother liquor was cooled, then 6N-hydrochloric acid was added to the mother liquor to adjust the pH thereof to pH 3-4. The crystals precipitated were colledted by filtration, washed with water, dried to obtain 45 g of 4-carboxycarbostyril.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureThen the reaction mixture was cooled a certain extent
  3. additionactivated carbon was added
  4. temperaturefurther refluxed for 30 minutes
  5. customThe activated carbon was removed from the reaction mixture by filtration while the mixture
  6. temperaturethe mother liquor was cooled
  7. addition6N-hydrochloric acid was added to the mother liquor
  8. customThe crystals precipitated
  9. filtrationwere colledted by filtration
  10. washwashed with water
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8102e89e9fcb42dfa9c3f4c409708163
Quelldatensatz
uspto-grants-1994_09
Patentnummer
USRE034722

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