反应 #586167

反应方程式

hydrogen

4,5-dimethoxy-2-[(4-ethoxy-1,4-dioxobutyl)amino]benzoic acid ethyl ester

N,N-dimethylformamide

sodium hydride

→

title compound

收率 57.8%

5-Hydroxy-7,8-dimethoxy-2-oxo-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester

收率 57.8%

溶剂

Brine

toluene

toluene

water

acetic acid

反应条件

后处理

1. 1
   温度cooled to 20° C.
2. 2
   干燥the organic phase dried (magnesium sulphate)
3. 3
   其他evaporated

实验过程

A solution of 4,5-dimethoxy-2-[(4-ethoxy-1,4-dioxobutyl)amino]benzoic acid ethyl ester (5.940 g, 16 mmol) and N,N-dimethylformamide (7.5 ml) in toluene (60 ml) was added dropwise to a stirred suspension of powdered sodium hydride (80%, 2.57 g, 85.7 mmol) under argon in toluene (70 ml). After the hydrogen evolution had ceased, the mixture was stirred for 7 hours at 80° C. under argon, then cooled to 20° C. and acetic acid (5 ml) and water (40 ml) added dropwise in succession. Brine (100 ml) was added and the organic phase dried (magnesium sulphate) and evaporated to give the title compound as a white solid, (2.842 g, 55% yield), mp 218° C.; 1H-NMR (DMSO-d6, 300 MHz): δ (ppm)=12.7 (br s; 1 H), 7.96 (s; 1H), 7.3 (s; 1H), 6.49 (s; 1H), 4.32 (q; 2H), 3.95 and 3.93 (s; 6H), 3.1 (s; 2H), 1.38 (t; 3H).

来源