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Synthesis method of isatoic anhydride and derivative thereof

A synthetic method, the technology of isatoic anhydride, applied in the direction of organic chemistry, etc., can solve the problems of serious equipment corrosion, not a synthetic method, etc., and achieve the effect of low equipment corrosion and high atom economy

Active Publication Date: 2014-06-11
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, under the existing technology, the reaction is often carried out under acidic conditions, which seriously corrodes the equipment, and is not an ideal synthesis method.

Method used

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  • Synthesis method of isatoic anhydride and derivative thereof
  • Synthesis method of isatoic anhydride and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015]

[0016] Add 1.47 g of isatin (10 mmol), 0.16 g of diphenyldiselenide (0.5 mmol) into a round bottom flask. Under stirring, keep the temperature of the mixed system at 25°C, and slowly add 25 ml of DMF-acetonitrile mixed solution (DMF volume content 10%) dissolved in 20 mmol mass concentration of 30% hydrogen peroxide solution dropwise. The mixture was stirred and reacted for 24 hours at a system temperature of 25°C.

[0017] After the reaction was completed, 30 ml of 5% ferrous chloride aqueous solution was added, extracted with ethyl acetate (50 ml 3 times), the organic layers were combined, dried with anhydrous sodium sulfate, evaporated to dryness, and the residue was separated by column chromatography to obtain indigo Red acid anhydride 1.39 g (yield 85%).

Embodiment 2

[0019] Other organoselenium catalysts were used to catalyze the reaction, and other conditions were the same as in Example 1. The experimental results are shown in Table 1.

[0020] Table 1 The reaction yields catalyzed by different organoselenium catalysts

[0021] serial number catalyst Yield(%) 1 diphenyl diselenide 85 (Example 1) 2 4,4'-Dimethoxydiphenyl diselenide 83 3 4,4'-Difluorodiphenyldiselenide 77 4 Dicyclohexyl diselenide 72 5 Benzene selenite 66 6 Phenylselenium bromide 70 7 diphenyl selenide 32 8 Phenylcyclohexylselenide 66

[0022] It can be seen from Table 1 that diphenyl diselenide is the best catalyst (Example 1).

Embodiment 3

[0024] Different amounts of diphenyldiselenide were used as catalysts, and other conditions were the same as in Example 1. The experimental results are shown in Table 2.

[0025] Table 2 Test of catalyst dosage effect:

[0026] serial number The amount of catalyst relative to isatin (mol%) Yield(%) 1 0.1 66 2 0.5 72 3 1 75 4 5 85 (Example 1) 5 10 83 6 15 78 7 20 73

[0027] It can be seen from Table 2 that the molar ratio of the catalyst relative to the amount of isatin is 1:20, and the effect is the best (Example 1).

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Abstract

The invention discloses a synthesis method of isatoic anhydride and a derivative thereof, relating to the technical field of chemical synthesis. In the presence of catalysis of an organic selenium catalyst, isatin or a derivative thereof is oxidized by using hydrogen peroxide to prepare the isatoic anhydride and the derivative thereof. The synthesis method disclosed by the invention is simple and easily available in raw materials, low in cost, clean in oxidizing agent, free from a metal catalyst, and environmentally friendly, can be carried out in a neutral environment, and is small in corrosion to equipment.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to the technical field of production of fine chemical products such as agricultural chemicals, dyes and medicines. Background technique [0002] Isatoic anhydride is widely used in the production of agricultural chemicals, dyes, pharmaceuticals and other fine chemical products. There are many synthetic methods of isatoic anhydride, among which obtaining isatoic anhydride by Baeyer-Vlliger oxidation of isatin is a common method. That is, under the action of an equivalent oxidant (usually peroxyacid, chromium trioxide, urea hydrogen peroxide complex, etc.), isatin oxidizes and opens the ring to form isatoic anhydride. However, these methods are not high in atom economy and will generate a lot of waste during use, which is not in line with the spirit of green chemistry. Hydrogen peroxide is a clean oxidant, and the reduction product after the reaction is water that is harm...

Claims

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Application Information

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IPC IPC(8): C07D265/26C07D413/04
CPCC07D265/26C07D413/04
Inventor 张旭李红艳俞磊叶剑青张明徐清
Owner YANGZHOU UNIV
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