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Synthetic method of 2-acetamido-5-chloropyridine

A synthesis method and acetamido technology, applied in the direction of organic chemistry, etc., can solve the problems of many by-products, complicated operation, troublesome operation, etc., and achieve the effects of stable product quality, mild reaction conditions, and easy operation.

Inactive Publication Date: 2017-05-10
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] (1) There are many by-products, resulting in a darker color of the product, which is difficult to refine and purify
Although it can be recrystallized multiple times with organic solvents, the quality still cannot meet the high requirements, and repeated crystallization leads to low product yield, increased cost, and cumbersome operation;
[0007] (2) The chemical reduction method used has serious corrosion of equipment and environmental pollution, and its development has been restricted at present;
[0008] (3) The source of raw materials is limited, the price is expensive, and the operation is troublesome

Method used

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  • Synthetic method of 2-acetamido-5-chloropyridine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 2-amino-5-chloropyridine (1.29g, 10mmol), acetic anhydride (1.53g, 15mmol) and 12ml of ethanol in a 50ml single-necked round bottom flask, start the magnetic stirrer, and the mixture in the reaction flask is at 75°C The reaction was stirred for 12 hours. TLC and GC detection confirmed that the reaction of the raw material 2-amino-5-chloropyridine was complete, water was added to the reaction solution, and then the reaction solution was suction-filtered, and the filter cake was recrystallized with ethyl acetate:n-hexane=1:4 to obtain the pure product 2- Acetylamino-5-chloropyridine, the filtrate was extracted with ethyl acetate, and the extractant was removed by rotary evaporation to obtain a crude product, which was then recrystallized with ethyl acetate:n-hexane=1:4 to obtain the pure product 2-acetylamino-5-chloropyridine Pyridine, after drying, calculated yield 65.37%, purity 98.61% (HPLC), nuclear magnetic resonance analysis: 1 HNMR (400Hz, deuterated DMSO) δ: ...

Embodiment 2

[0027] Add 2-amino-5-chloropyridine (1.29g, 10mmol), acetic anhydride (1.02g, 10mmol) and 10ml of tert-butanol in a 50-ml single-necked round-bottomed flask, start the magnetic stirrer, and the mixture in the reaction flask is The reaction was stirred at 75°C for 12 hours. TLC and GC detection confirmed that the reaction of the raw material 2-amino-5-chloropyridine was complete, water was added to the reaction solution, and then the reaction solution was suction-filtered, and the filter cake was recrystallized with ethyl acetate:n-hexane=1:4 to obtain the pure product 2- Acetylamino-5-chloropyridine, the filtrate was extracted with ethyl acetate, and the extractant was removed by rotary evaporation to obtain a crude product, which was then recrystallized with ethyl acetate:n-hexane=1:4 to obtain the pure product 2-acetylamino-5-chloropyridine Pyridine, after drying, calculated yield 65.30%, purity 99.00% (HPLC).

Embodiment 3

[0029] Add 2-amino-5-chloropyridine (12.86g, 100mmol), acetic anhydride (15.30g, 150mmol) and 160ml of ethanol in a 500ml single-necked round bottom flask, start the magnetic stirrer, and the mixture in the reaction flask is at 75°C The reaction was stirred for 11 hours. TLC and GC detection confirmed that the reaction of the raw material 2-amino-5-chloropyridine was complete, water was added to the reaction solution, and then the reaction solution was suction-filtered, and the filter cake was recrystallized with ethyl acetate:n-hexane=1:4 to obtain the pure product 2- Acetylamino-5-chloropyridine, the filtrate was extracted with ethyl acetate, and the extractant was removed by rotary evaporation to obtain a crude product, which was then recrystallized with ethyl acetate:n-hexane=1:4 to obtain the pure product 2-acetylamino-5-chloropyridine Pyridine, after drying, calculated yield 70.38%, purity 99.53% (HPLC).

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Abstract

The invention relates to a synthetic method of 2-acetamido-5-chloropyridine. The synthetic method comprises the following steps: making 2-amino-5-chloropyridine and acetic anhydride which are taken as raw materials continuously react in a mass ratio of 1 to (1.0-3.2) in a proper solvent at the temperature of 50 to 110 DEG C for 4 to 15 hours to generate a 2-amino-5-chloropyridine rough product; purifying to obtain a 2-amino-5-chloropyridine pure product. In the synthetic method, the raw materials are readily-available, and are reasonable in costs; meanwhile, in the preparation process, heavy metal and corrosive gas are not used, the reaction is mild, special requirements on reaction equipment are avoided, and ordinary corrosion-resistant equipment can be used for producing; moreover, the synthetic method is moderate in reaction conditions, and does not cause no any environmental pollution.

Description

[0001] (1) Technical field [0002] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 2-acetylamino-5-chloropyridine. [0003] (2) Background technology [0004] As a bromopyridine derivative, 2-acetylamino-5-chloropyridine is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, organic solvents, and can also be used in dye production, pesticide production and spices etc. [0005] The preparation of existing pyridine bromide has the following disadvantages: [0006] (1) There are many by-products, resulting in a darker color of the product, which is difficult to refine and purify. Although organic solvents can be used to recrystallize multiple times, the quality still cannot meet the high requirements, and repeated crystallization leads to low product yield, increased cost, and cumbersome operation; [0007] (2) The chemical reduction method used has serious c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/75
CPCC07D213/75
Inventor 耿宣平来超来子腾来新胜
Owner SHANDONG YOUBANG BIOCHEM TECH