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A kind of isatin derivative and its synthetic method

A synthetic method and derivative technology, applied in the direction of organic chemistry, can solve the problem of lower yield of target product, achieve the effect of reducing by-product generation, increasing yield, and simple synthesis route

Inactive Publication Date: 2018-10-30
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the existing synthetic technology, diphenylamine is basically used as the substrate raw material, oxalyl chloride is added to react to obtain an intermediate, and then N-phenyl isatin is catalyzed by anhydrous aluminum trichloride, but after a series of chemical synthesis steps , produced a lot of by-products, especially diphenylamine and oxalyl chloride generate the by-products with the following structure, which greatly reduces the yield of the target product

Method used

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  • A kind of isatin derivative and its synthetic method
  • A kind of isatin derivative and its synthetic method
  • A kind of isatin derivative and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] when R 1 When it is phenyl, product name: N-phenylisatin

[0034]

[0035] Weigh N-phenylindolinone 1mmol (209mg) into a 100mL round-bottomed flask, measure 15ml of dioxane with a graduated cylinder and add it to the round-bottom flask, then add 1mmol (111mg) of selenium dioxide ( SeO 2 ), heated to reflux in an oil bath at 130 °C, and the reaction system continued for 10 h after heating and cooling to room temperature.

[0036] Subsequently, dioxane in the reaction system was removed by rotary evaporation, and 20 ml of ethyl acetate was added to the reaction system to dissolve the target product, followed by extraction twice with a separating funnel, the organic phases were combined, and anhydrous magnesium sulfate was added to dry. Finally, silica gel was added and spun into dry powder and applied to the column, and the mixture of ethyl acetate and petroleum ether was passed through the column to obtain 200.7 mg of N-phenylisatin as a brick-red solid with a yield...

Embodiment 2

[0041] when R 1 When it is methyl, product name: N-methylisatin

[0042]

[0043] In the experiment, the previously added N-phenylindolinone was replaced with N-methylindolinone, and the remaining steps were the same as in Example 1 to obtain a red solid with a yield of 84%.

[0044] 1 H NMR (400MHz, CDCl 3 )δ7.70–7.55(m,1H),7.14(t,J=7.5Hz,1H),6.91(d,J=7.9Hz,1H),3.26(s,1H). 13 C NMR (101MHz, CDCl 3 )δ183.35(s), 158.25(s), 151.47(s), 138.43(s), 125.26(s), 123.84(s), 117.45(s), 109.95(s), 26.22(s).

Embodiment 3

[0046] when R 1 When it is ethyl, product name: N-ethylisatin

[0047]

[0048]In the experiment, the previously added N-phenylindolinone was replaced with N-ethylindolinone, and the remaining steps were the same as in Example 1 to obtain a red solid with a yield of 85%.

[0049] 1 H NMR (400MHz, CDCl 3 )δ7.66–7.55(m,2H),7.12(td,J=7.6,0.5Hz,1H),6.95(d,J=7.9Hz,1H),3.79(q,J=7.2Hz,2H), 1.32(t,J=7.2Hz,3H). 13 C NMR (101MHz, CDCl 3 )δ183.96(s), 158.12(s), 150.88(s), 138.71(s), 125.61(s), 123.89(s), 117.80(s), 110.39(s), 35.20(s), 12.75( s).

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Abstract

The invention relates to an isatin derivative and a synthetic method thereof. The synthetic method comprises the following steps: adding N-substituted indolinone into a solvent first, then adding an oxidant, and performing a reaction in an oil bath at 90-140 DEG C until a reaction system changes from clear liquid into reddish brown liquid;removing the solvent from the reaction system to obtain a crude product, performing extraction and separation on the crude product sequentially to obtain the isatin derivative. In the synthetic method provided by the invention, the N-substituted indolinone is used as a raw material and contains a methylene in a molecule, and a phenyl at a position adjacent to the methylene, so that under the action of the oxidant, the benzyl methylene can form a stable intermediate more possibly, and by matching with reaction temperature control, N-phenyl indolinone is oxidized into a target product namely the isatin derivative under the action of the oxidant, byproducts are effectively reduced, and finally the isatin derivative is purified by extraction and separation. The isatin derivative provided by the invention has a simple synthesis route, the steps are simplified, the generation of the byproducts is effectively avoided, an atom efficiency is fully utilized, and the yield of the isatin derivative is improved.

Description

【Technical field】 [0001] The invention belongs to the field of organic synthesis, in particular to an isatin derivative and a synthesis method thereof. 【Background technique】 [0002] Isatin derivatives play an important role in organic synthesis. They can not only be used as dyes and pharmaceutical intermediates, but also can be used to produce drugs such as Cincophen and Dye Disperse Yellow E-3G. Among them, N-phenylisatin can also be used in chemiluminescence immunoassays. Synthesis of Reagents. Chemiluminescence Immunoassay (CLIA), as a new type of labeled immunoassay technology, is applied to the detection of trace antibodies or antigens. Compared with radioimmunoassay (also known as RIA) and enzyme immunoassay (also known as EIA), this analytical method has obvious advantages: simple operation, high sensitivity, rapid and easy standardization, and no radioactive substances are generated during the experiment. CLIA detection technology has developed various types of c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/38
CPCC07D209/38
Inventor 王林玉姚曼文方湘怡姚熹
Owner XI AN JIAOTONG UNIV
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