Dimethylformamide → 6-Chloro-5-nitro-1H-isochromen-1-one

Participants

Reaction Conditions

Reaction Steps

A pressure tube was charged with methyl 4-chloro-2-methyl-3-nitrobenzoate (13 g, 57 mmol), N,N-dimethylformamide (10 mL, 200 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (26.5 mL, 200 mmol). The reaction was heated at 120° C. for 20 h. The solvents were removed and the resultant brown residue was redissolved in ethyl acetate (600 mL, 6000 mmol) and 130-270 mesh 60A silica gel (500 g, 6000 mmol) was added. The reaction was stirred with a mechanical stirrer for 8 h. The reaction was filtered, washed with ethyl acetate (400 mL). the organics were combined. and the solvents were removed under reduced pressure. The residue was purified by flash chromatography to give the desired product.

Provenance & Evidence