Reacción #2195492

Ecuación de reacción

N-methylisatoic anhydride

HCl

ethylmethanesulfonylacetate

sodium hydride

hydrogen

→

white solids

Rendimiento 48.0%

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

Rendimiento 48.0%

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 ethylmethanesulfonylacetate (3.78 g, 22.74 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 1.07 g, 25 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 (4.43 g, 25 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 2.76 g (48%) of white solids. Mp 170° C. 1H NMR (DMSO-d6): δ 3.51 (s, 3H), 3.59 (s, 3H), 7.39 (t, J=7.4 Hz, 1H), 7.62 (d, J=8.5 Hz, 1H), 7.84 (t, J=7.0 Hz, 1H), 8.09 (d, J=8.0 Hz, 1H). EIMS m/z 254 (M+1), 276 (M+23). Anal. (C11H11NO4S) C, H, N.

Fuente