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

Participants

Reaction Conditions

Reaction Steps

Methyl 2-methyl-3-nitrobenzoate (5 g, 0.02 mol) and 1,1-dimethoxy-N,N-dimethylmethanamine (10 mL, 0.07 mol) were dissolved in N,N-dimethylformamide (30 mL, 0.4 mol). The mixture was stirred at 115° C. for 17 hours. The volatiles were removed on a rotavapor. The residue was dissolved in ethylacetate (400 mL) and then silica gel (400 g) was added. The mixture was stirred at room temperature for 3 hours. Filtered, rinsed with ethylacetate (400 mL×3). Combined filtrates were concentrated to dryness to get a brown solid (3.6 g). MS m/z=192.0 (M+1).

Provenance & Evidence