2-Cyanobenzoic acid → 6-Amino-2,3-dihydro-3,3-dimethyl-1H-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

3,3-Dimethylisoindolin-1-one. 2-Cyanobenzoic acid (3 g, 20.39 mmol) was dissolved in tetrahydrofuran (300 mL) and then cooled to −78° C. Methyllithium (127 mL, 204 mmol) was added dropwise and the reaction was slowly warmed to room temperature over 2 hours. The reaction was quenched with brine then extracted twice with ethyl acetate. The combined organics were washed with 1 N HCl, saturated sodium bicarbonate and water, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography to give the desired product. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 8.58-8.69 (m, 1H), 7.53-7.66 (m, 3H), 7.45 (dd, J=1.56, 7.42 Hz, 1H), 1.44 (s, 6H). MS (ESI) m/z 162.2 [M+1]+.

Provenance & Evidence