反应 #2195489

反应方程式

N-methylisatoic anhydride

HCl

ethylnitroacetate

sodium hydride

hydrogen

→

yellow solids

收率 27.0%

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

收率 27.0%

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 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.

来源