反应 #2195492

反应方程式

N-methylisatoic anhydride

HCl

ethylmethanesulfonylacetate

sodium hydride

hydrogen

→

white solids

收率 48.0%

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

收率 48.0%

溶剂

dimethylacetamide

dimethylacetamide

反应条件

后处理

1. 1
   温度cooled to room temperature
2. 2
   温度heated overnight at 120° C
3. 3
   温度The mixture was cooled to room temperature
4. 4
   其他The solids formed
5. 5
   过滤were filtered
6. 6
   洗涤washed several times by water

实验过程

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.

来源