Phenol → Phenyl acridine-9-carboxylate

HRID 2395921

Reaktionsgleichung

Reaktionsgleichung von HRID 2395921
[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.N1C=CC=CC=1.[C:24]1(O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>S(Cl)(Cl)=O.C(Cl)Cl>[CH:11]1[C:12]2[C:7](=[N:6][C:5]3[C:14]([C:13]=2[C:15]([O:17][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:16])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Komponenten

6

Edukt 3

HCID 996PhenolHCID 1049PyridineHCID 94721Acridine-9-carboxylic acid

Produkt 1

HCID 517916Phenyl acridine-9-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

Acridine-9-carboxylic acid (1 g, 4.1 mmol) was suspended in thionyl chloride (5 mL) and the reaction mixture was refluxed for 3 hours. The solvent was removed under reduced pressure leaving a yellow solid which was dissolved in methylene chloride and pyridine (350 μL) under argon. This solution was cooled in an ice bath and a solution of phenol (0.78 g, 8.2 mmol) in methylene chloride was added dropwise. The reaction mixture was stirred overnight at room temperature. After evaporation of solvent, the residue was redissolved in ethyl acetate and washed with water. The organic layer was dried over MgSO4 and concentrated to obtain a crudematerial which was chromatographed on silica gel (30% ethyl acetate/hexane)to yield the pure product as a yellow solid. 1H NMR (CDCl3) δ7.35-7.57 (m, 5H), 7.63-8.37 (m, 8H).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. customleaving a yellow solid which
  4. temperatureThis solution was cooled in an ice bath
  5. customAfter evaporation of solvent
  6. dissolutionthe residue was redissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated
  10. customto obtain a crudematerial which
  11. customwas chromatographed on silica gel (30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-18073fa1fa044b4ba7e65bd405adcda3
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05491072

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