Hydrochloric Acid → 2-(4-Fluorophenyl)quinoline-4-carboxylic acid

HRID 638269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638269
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[OH-:12].[Na+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH3:22])=[CH:17][CH:16]=1.Cl>C(O)C>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:4]([C:2]([OH:12])=[O:3])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:1]=2)=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7054IsatinHCID 98284'-FluoroacetophenoneHCID 14798Sodium Hydroxide

Produkt 1

HCID 7231632-(4-Fluorophenyl)quinoline-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 36.78 g (0.25 mol) of isatin in 500 ml of ethanol was added 75 ml of 10N sodium hydroxide. After a few minutes of stirring a solid precipitated. To this mixture was added 35 ml (0.286 mol) of p-fluoroacetophenone, and it was stirred and heated under reflux for 1.5 hr. It was then allowed to cool slightly, and acidified with 250 ml of 3N hydrochloric acid. The precipitated solid was collected, washed with water and with ether, and dried to give 50.6 g of crude product, mp 205-215. Recrystallization from ethanol gave 38.8 g of the above-named acid, mp 210°-213° dec.

Aufarbeitung

  1. customprecipitated
  2. stirringwas stirred
  3. temperatureheated
  4. temperatureunder reflux for 1.5 hr
  5. temperatureto cool slightly
  6. customThe precipitated solid was collected
  7. washwashed with water and with ether
  8. customdried
  9. customto give 50.6 g of crude product, mp 205-215
  10. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-77d40bc9282c4196a7917222bc6dc228
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560692

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