Ethyl Acetate → 2-[3-(3-Chloro-phenyl)-propyl]-2,3-dihydro-isoindol-1-one

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Reaction Conditions

Reaction Steps

A mixture of 2-bromomethyl-benzoic acid methyl ester (0.115 g, 0.5 mmol), 3-(3-chloro-phenyl)-propylamine (0.102 g, 0.6 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (3 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-[3-(3-chloro-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.105 g, 71%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.96 (m, 2H), 2.69 (t, 2H), 3.66 (t, 2H), 4.36 (s, 2H), 7.12-7.58 (m, 7H), 7.84 (d, 1H). GC-MS: m/z 285 (M)+.

Provenance & Evidence