Dimethylformamide → 4-Methoxy-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one

Participants

Reaction Steps

A mixture of 4-Hydroxy-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one (Compound 205C, 50.0 mg, 0.240 mmol), potassium carbonate (49.8 mg, 0.360 mmol) in DMF (2 mL, 20 mmol) was treated with methyl iodide (22.4 μL, 0.360 mmol) and allowed to stir at room temperature overnight. The reaction was poured into EtOAc and washed with water and brine and the crude material was purified using an ISCO Combiflash unit (MeOH in DCM: 0-1%) to obtain the title product as a solid. (27 mg, 50% yield). 1H NMR (400 MHz, CD3OD) δ=3.17 (s, 3 H), 4.02 (s, 3 H), 4.44 (s, 2 H), 7.27 (d, J=8.8 Hz, 1 H), 7.94 (d, J=8.8 Hz, 1 H). MS (ES+): m/z 223.19 (100) [MH+]; HPLC: tR=0.76 min (UPLC, analytical).

Provenance & Evidence