Hydrochloric Acid → Phenyl acridine-9-carboxylate

HRID 440631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 440631
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.Cl>S(Cl)(Cl)=O>[CH:11]1[C:12]2[C:7](=[N:6][C:5]3[C:14]([C:13]=2[C:15]([O:17][C:1]2[CH:14]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:16])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 94721Acridine-9-carboxylic acid

Produkt 1

HCID 517916Phenyl acridine-9-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

Acridine-9-carboxylic acid (5 g) is suspended in thionyl chloride (75 ml). The mixture is stirred under reflux for four hours. The excess of thionyl chloride is removed by distillation. The residue is suspended in pyridine (75 ml) and the mixture stirred at room temperature for ten minutes. Phenol (4.5 g) is added to the suspension. The resulting reaction mixture is stirred at room temperature for sixteen hours. The resulting solution is poured into one normal hydrochloric acid (200 ml). The precipitate that forms (6.5 g) is isolated by filtration, and recrystallized from benzene/cyclohexane. m.p. 192° C.; IR (KBr): 1750, 1177 cm-1. MS: 299, 206, 178, 152, 151. 1H-NMR: δ7.5-8.5.

Aufarbeitung

  1. temperatureunder reflux for four hours
  2. customThe excess of thionyl chloride is removed by distillation
  3. stirringthe mixture stirred at room temperature for ten minutes
  4. additionPhenol (4.5 g) is added to the suspension
  5. customThe resulting reaction mixture
  6. stirringis stirred at room temperature for sixteen hours
  7. customis isolated by filtration
  8. customrecrystallized from benzene/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-9b5c4b491dea4951973095daa0509580
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521103

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