Toluene → N-(2-Naphthylmethyl)phthalimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of naphthalen-2-yl-methylamine (47.2 mg, 0.3 mmol), 2-bromomethyl-benzoic acid methyl ester (68.7 mg, 0.3 mmol), and K2CO3 (83 mg, 0.6 mmol) in toluene (2 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using a gradient of hexanes to 50% ethyl acetate in hexanes afforded 2-naphthalen-2-ylmethyl-2,3-dihydroisoindol-1-one (57 mg, 70%). GC/MS gave: m/z (rel.int.) 273 (M+, 45), 141 (100), 119 (27), 115 (27), and 91 (25).

Provenance & Evidence