Methyl 4-cyano-2-methylbenzoate → 1-Oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

methyl 4-cyano-2-methylbenzoate. To a stirred solution of methyl 4-bromo-2-methylbenzoate (2 g, 8.7 mmol) in DMF (20 mL), was added CuCN (1.9 g, 12.2 mmol). The reaction was then stirred at 175° C. for 6 h. The progress of the reaction was monitored by TLC (10% EtOAc in hexanes). The reaction was diluted with EtOAc (10 mL) and filtered through Celite® brand filtering agent. The filtrate was concentrated in vacuo and the material was purified by column chromatography (SiO2, 0-50% EtOAc in hexanes) to give the title compound. MS (ESI pos. ion) m/z: 177.1 (MH+).

Provenance & Evidence