反応 #2195492

反応方程式

N-methylisatoic anhydride

HCl

ethylmethanesulfonylacetate

sodium hydride

hydrogen

→

white solids

収率 48.0%

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

収率 48.0%

溶媒

dimethylacetamide

dimethylacetamide

反応条件

後処理

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
   その他The solids formed
5. 5
   ろ過were filtered
6. 6
   洗浄washed several times by water

実験手順

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.

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