N-Carbethoxyphthalimide → 2-[(3,4-Dimethoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione

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Reaction Steps

To a stirred solution of 3,4-dimethoxybenzylamine (0.836 grams, 5.00 mmol) and N-carbethoxyphthalimide (1.10 grams, 5.00 mmol) in 20 milliliters of tetrahydrofuran was added 1 drop of triethylamine and the mixture stirred overnight. After 24 hours at room temperature, the mixture was refluxed for 16 hours, then allowed to cool to room temperature without stirring. Crystals formed on cooling. The mixture was filtered, the solid dried in vacuo to afford 0.89 grams (60%) of 1-phthalimido-1-(3′,4′-dimethoxyphenyl)methane as small white needles: mp 160-161° C.; 1H NMR (CDCl3/TMS) δ 7.8 (m, 2H), 7.7 (m, 2H), 7.03 (m, 2H), 6.8 (m, 1H), 4.78 (s, 2H), 3.88 (s, 3H, OCH3), 3.84 (s, 3H, OCH3); 13C NMR (CDCl3/TMS) δ 168.0, 148.9, 148.7, 133.9, 132.1, 129.0, 123.3, 121.3, 112.1, 111.1, 55.9, 41.4. Anal. Calcd for C17H15NO4. Theory: C, 68.68; H, 5.09; N, 4.71. Found: C, 68.49; H, 4.99; N, 4.67.

Provenance & Evidence