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Preparation method for 6-bromine quinoline

The technology of bromoquinoline and p-bromoaniline is applied in the field of preparation of 6-bromoquinoline, can solve the problems of high finished product, difficult recovery of solvent, complicated reaction steps and the like, and achieves the effects of simple and convenient operation, low price and low finished product

Inactive Publication Date: 2016-08-10
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method prepares 6-bromoquinoline compound reaction comparatively mildly, but finished product is on the high side, the solvent is difficult to recycle, and the disadvantages such as loaded down with trivial details of reaction steps

Method used

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  • Preparation method for 6-bromine quinoline
  • Preparation method for 6-bromine quinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) Put 0.1mol of p-bromoaniline, 0.43mol of sulfuric acid (concentration 80%), and 0.006mol of potassium iodide into the reaction bottle, heat up to 140-145°C, heat and stir until completely dissolved, and control the internal temperature of 140-145°C to the bottle Add 0.125 mol of glycerol dropwise. During the dropping process, water will be evaporated. After the dropping is completed, dehydrate at 140-145°C for 3 hours to check whether there are any raw materials remaining. The product has a purity of 85.4%, and quinoline is 10.2% (GC);

[0020] (2) Drop the reaction solution from the previous step into water, and adjust the pH to 6-7 with 0.35 mol of ammonia water;

[0021] (3) Add 200ml toluene to the upward step reaction solution for extraction and layering, then extract the aqueous phase twice with 200ml toluene, extract toluene and concentrate to obtain black 6-bromoquinoline crude product, purity 92%, quinoline 4% (HPLC). Control vacuum ≤ 15mmHg, collect 150~15...

Embodiment 2

[0023] (1) Put 0.1mol p-bromoaniline, 0.43mol sulfuric acid (concentration 70%), and 0.006mol potassium iodide into the reaction bottle, heat up to 140-145°C, heat and stir until they are completely dissolved, and control the internal temperature of 140-145°C to the bottle Add 0.125 mol of glycerol dropwise. During the dropwise addition, water will be evaporated. After the dropwise addition, dehydrate at 140-145°C for 3 hours to detect 1.7% of raw material residue, product purity 79.4%, and quinoline 12.8% (GC);

[0024] (2) Drop the reaction solution from the previous step into water, and adjust the pH to 6-7 with 0.35 mol of ammonia water;

[0025] (3) Add 200ml of toluene to the upward step reaction solution for extraction and layering, then extract the water phase twice with 200ml of toluene, extract the toluene and concentrate to obtain black 6-bromoquinoline crude product, purity 87.3%, quinoline 7.5% (HPLC). Control vacuum ≤ 15mmHg, collect 150~155 ℃ distillate, the 6-b...

Embodiment 3

[0027] (1) Put 0.1mol p-bromoaniline, 0.43mol sulfuric acid (concentration 90%), and 0.006mol potassium iodide into the reaction bottle, heat up to 140-145°C, heat and stir until they are completely dissolved, and control the internal temperature of 140-145°C to the bottle Add 0.125 mol of glycerol dropwise. During the dropwise addition, water will be evaporated. After the dropwise addition, dehydrate at 140-145°C for 3 hours to detect 0% of the raw material residue, product purity 75.4%, and quinoline 19.8% (GC);

[0028] (2) Drop the reaction solution from the previous step into water, and adjust the pH to 6-7 with 0.35 mol of ammonia water;

[0029] (3) Add 200ml of toluene to the upward step reaction solution for extraction and layering, and the aqueous phase is extracted twice with 200ml of toluene, and the extraction toluene is combined and concentrated to obtain black 6-bromoquinoline crude product with a purity of 84%, quinoline 10.9% (HPLC). Control vacuum ≤ 15mmHg, c...

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Abstract

The invention discloses a preparation method for 6-bromine quinoline and relates to the technical field of organic synthesis. A catalyst and parabromoaniline are added into dilute sulphuric acid, the temperature of 140-145 DEG C is controlled, glycerol is dropwise added, and after dropping adding, 140-145 DEG C dehydration reaction is conducted for 3 h; the reaction liquid is dropwise added into ice water, then, ammonium hydroxide is added dropwise, and pH of a system is adjusted; methylbenzene is used for extracting the reaction liquid, methylbenzene-phase concentration is 150-155 DEG C / 15 mmHg, the obtained crude product is distilled, and then the product 6-bromine quinoline is obtained. A catalytic number of catalysts are adopted as the reaction raw materials, the price of the catalyst is lower than that of other oxidizing agents, waste water and exhaust gas are treated easily, and no waste residue is produced. Finished raw material products are low in price, the recovery rate of adopted solvent is high, one-pot method operation is easy and convenient, and the yield is greatly increased.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 6-bromoquinoline. Background technique: [0002] 6-Bromoquinoline is a structural fragment of important physiologically active substances, and is widely used in the synthesis of pharmaceutical intermediates, such as in the synthesis of anticancer drug enhancers, receptor tyrosine kinase inhibitors and cardiotonic agents. Although the current market demand is very large, there is no detailed report on its synthesis method at home and abroad. [0003] Sun Qingbin.Study on the synthesis process of 6-bromoquinoline[J].Guangzhou Chemical Industry, 2011,39-15:115-116 discloses a preparation method of 6-bromoquinoline. It uses p-bromoaniline and glycerol in a sulfuric acid system, adding nitrobenzene and ferrous sulfate for reflux reaction, after the reaction is completed, adjust the pH to 5-6 with 50% sodium hydroxide, and filter out iron salts and o...

Claims

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Application Information

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IPC IPC(8): C07D215/18
CPCC07D215/18
Inventor 杨青魏佳玉赵士民徐剑霄
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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