[CH:1]1[C:10]2C(=CC=CC=2)C=C[C:2]=1[NH:11]C.CO[C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22]Br.[C:25]([O-:28])([O-])=O.[K+].[K+].C(OCC)(=O)C.[C:37]1([CH3:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH:22]1[C:17]2[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:10][C:1]=1[CH2:2][N:11]1[CH2:43][C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:25]1=[O:28]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).
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