反応 #2195489

反応方程式

N-methylisatoic anhydride

HCl

ethylnitroacetate

sodium hydride

hydrogen

→

yellow solids

収率 27.0%

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

収率 27.0%

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 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.

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