Hydrochloric Acid → Phenyl acridine-9-carboxylate

HRID 850697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 850697
[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-d4b67d0f369b46dfa699e9a20039c9c4
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06018047

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