Phenol → Phenyl acridine-9-carboxylate

Beteiligte Stoffe

Reaktionsschritte

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).

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