反应 #213867

反应方程式

6-chloro-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid

2-mercaptobenzoic acid

potassium carbonate

→

title compound

收率 64.0%

1,3-Dioxo-6-[(2-carboxyphenyl)thio]-1H-benz[de]isoquinoline-2(3H)-acetic acid

收率 64.0%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   温度at reflux for 3 hr
2. 2
   其他The product in the form of its sodium salt was precipitated from the reaction mixture
3. 3
   过滤The precipitate was collected by filtration
4. 4
   workup.DISSOLUTIONdissolved in water
5. 5
   其他The resulting precipitate was collected
6. 6
   其他dried
7. 7
   其他crystallized from dimethylformamide and water

实验过程

A mixture of 6-chloro-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid (10.0 g, 34.5 mmoles, described in Example 2); 2-mercaptobenzoic acid (5.85 g, 37.9 mmoles) and anhydrous potassium carbonate (9.54 g, 37.9 mmoles) in dimethylformamide (300 ml) was heated at reflux for 3 hr. The product in the form of its sodium salt was precipitated from the reaction mixture. The precipitate was collected by filtration and dissolved in water. The solution of the sodium salt was rendered acidic with 2 N hydrochloric acid. The resulting precipitate was collected, dried and crystallized from dimethylformamide and water to give 9.0 g of the title compound; mp 339°-341° C.; UV (MeOH) 231, 254, 336 and 346, ε=31,450, 15,810, 8,760 and 9,210, respectively; IR (CHCl3) 2900, 1725, 1710, 1675 cm-1 ; NMR (CDCl3) δ 4.7 (s, 2H), 6.5-8.6 (m, 9H), 13.0 (broad, 1H); Anal. Calc'd: C, 61.91%; H, 3.22%; N, 3.44%; Found: C, 61.51%; H, 3.21%; N, 3.73%.

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