Reacción #2195489

Ecuación de reacción

N-methylisatoic anhydride

HCl

ethylnitroacetate

sodium hydride

hydrogen

→

yellow solids

Rendimiento 27.0%

4-Hydroxy-1-methyl-3-nitro-1H-quinolin-2-one

Rendimiento 27.0%

Disolventes

dimethylacetamide

dimethylacetamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Temperaturaheated overnight at 120° C
3. 3
   TemperaturaThe mixture was cooled to room temperature
4. 4
   OtroThe solids formed
5. 5
   Filtraciónwere filtered
6. 6
   Lavadowashed several times by water

Procedimiento

A solution of ethylnitroacetate (15.96 g, 120 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 5.28 g, 132 mmol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min. and cooled to room temperature. A solution of N-methylisatoic anhydride (23.38 g, 132 mmol) in dimethylacetamide was added slowly and heated overnight at 120° C. The mixture was cooled to room temperature, poured into ice water, and acidified by cold 10% HCl. The solids formed were filtered and washed several times by water to yield 7.1 g (27%) of yellow solids. Mp 193° C. 1H NMR (DMSO-d6): δ 3.60 (s, 3H), 7.37 (t, J=7.6 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.77 (t, J=7.5 Hz, 1H), 8.12 (d, J=7.9 Hz, 1H). EIMS m/z 221 (M+1), 243 (M+23). Anal. (C10H8N2O4) C, H, N.

Fuente