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ChemicalBook CAS DataBase List N-Chlorophthalimide
3481-09-2

N-Chlorophthalimide synthesis

3synthesis methods
1H-Isoindol-1-one, 3-hydroxy-

136918-14-4

N-Chlorophthalimide

3481-09-2

General procedure for the synthesis of N-chlorophthalimide from 3-hydroxy-1H-isoindol-1-one: Anhydrous aluminum trichloride (AlCl3, 1 eq., 10 mmol, 1.36 g) was added to an anhydrous acetonitrile (CH3CN, 100 mL) solution of lead tetraacetate (Pb(OAc)4, 1 eq., 10 mmol, 4.52 g). The mixture was stirred at room temperature for 5 minutes before phthalimide (1 eq., 10 mmol, 1.5 g) was added. The resulting mixture was gently refluxed under nitrogen protection for 20 h and subsequently cooled to room temperature. The solvent was removed by rotary evaporation and the crude product was purified by column chromatography using pure dichloromethane (DCM) as eluent. Yield: 1.32 g, 71% yield.1H NMR (300 MHz, CDCl3): δ 7.94-7.91 (m, 2H), 7.82-7.79 (m, 2H) ppm.

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