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Method for synthesizing 3,5-diiodo-4-aminopyridine by employing in-situ iodized reagent production method

A technology of aminopyridine and synthesis method, which is applied in the field of synthesis of iodoaminopyridine, can solve the problems of instability of iodine chloride, easy blockage of condensation pipe, low reaction yield, etc., and achieve good economic and social benefits and process operation Simple process and high reaction selectivity

Inactive Publication Date: 2015-01-07
XIHUA UNIV
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Problems solved by technology

Because this method uses iodine chloride as the iodination reagent, not only the price is high, but also the iodine chloride is extremely unstable, and the reaction yield is low. It belongs to the early synthesis method like method 2 and has no industrial application value.
[0007] In summary, the prior art has the disadvantages of difficult and expensive synthesis using special iodination reagents (method 3), or the starting raw materials are not easy to obtain, the price is high, and the reaction yield is low (method 2), or there is iodination The iodine elemental substance of the reagent is very easy to sublime, which not only affects the normal progress of the reaction process, but also easily blocks the condensation tube, which has the disadvantages of potential safety hazards (method 1), which makes the prior art have many technical problems that need to be solved for such or such large-scale production

Method used

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  • Method for synthesizing 3,5-diiodo-4-aminopyridine by employing in-situ iodized reagent production method
  • Method for synthesizing 3,5-diiodo-4-aminopyridine by employing in-situ iodized reagent production method
  • Method for synthesizing 3,5-diiodo-4-aminopyridine by employing in-situ iodized reagent production method

Examples

Experimental program
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Effect test

Embodiment 1

[0031] In the reaction flask, add 500 mL of methanol, 3000 mL of water, 94.11 g (1.0 mol) of 4-aminopyridine, 224.10 g (1.35 mol) of potassium iodide, and 149.80 g (0.70 mol) of potassium iodate in sequence, and slowly drop them at 20°C Concentrated hydrochloric acid 160mL, it takes 3 hours to add dropwise, continue to stir and react for 1 hour after dropwise addition, then drop into 50mL aqueous solution containing 17.73g (0.20mol) of sodium chlorite, continue to stir and react for 0.5 hour after dropwise addition, high efficiency After the liquid chromatography central control monitors the reaction, the reaction solution is diluted with 4000mL of water, and 6000mL of extractant trichloromethane is added three times, and the combined organic phase is washed once with brine containing sodium thiosulfate and sodium bicarbonate containing Wash once with salt water, separate the phases, dry over anhydrous magnesium sulfate, and remove the solvent chloroform under reduced pressure ...

Embodiment 2

[0033] In the reaction described in Example 1, 201.02 g (1.35 mol) of sodium iodide was substituted for 224.10 g (1.35 mol) of potassium iodide, and other operations were the same as in Example 1.

[0034] According to the operation of Example 1, 303.36 g of white crystalline solid 3,5-diiodo-4-aminopyridine was obtained, with a yield of 87.7% and a relative liquid phase content of 98.3%.

Embodiment 3

[0036] In the reaction described in Example 1, the amount of potassium iodate used was 256.80 g (1.20 mol), and other operations were the same as in Example 1.

[0037]The operation was carried out according to Example 1, and 315.47 g of white crystalline solid 3,5-diiodo-4-aminopyridine was obtained, with a yield of 91.2% and a relative liquid phase content of 98.9%.

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Abstract

The invention discloses synthesis of 3,5-diiodo-4-aminopyridine by employing an in-situ iodized reagent production method. 4-aminopyridine, iodized salt, potassium iodate and sodium chlorite are taken as main reaction materials; in a reaction process, an oxidant slowly oxidizes the iodized salt into iodine required in reaction; and reaction is carried out in an in-site iodine production manner to obtain the target product 3,5-diiodo-4-aminopyridine. Compared with an existing public technology, the process route has the characteristics that reaction selectivity is high, the quality of the obtained product is high, the iodized reagent is low in price, and the technological operation process is simple.

Description

[0001] technical field [0002] The invention relates to a method for synthesizing iodoaminopyridine, in particular to a method for synthesizing 3,5-diiodo-4-aminopyridine. Background technique [0003] 3,5-diiodo-4-aminopyridine is widely used in the fields of pharmaceutical intermediates, fine chemicals, pesticides, chemical reagents and the like because it contains both iodine substituents and active amino substituents. In recent years, many documents have reported the use of 3,5-diiodo-4-aminopyridine. For example, literature ( Chemistry - A European Journal ; vol. 18; nb. 5; (2012); p. 1306 - 1310) announced the synthesis of azo compound derivatives with redox activity using 3,5-diiodo-4-aminopyridine as an important intermediate. literature( Journal of the American Chemical Society ; vol. 126; nb. 9; (2004); p. 2807 - 2819) published the alkynylation of various alkynyl compounds with 3,5-diiodo-4-aminopyridine. literature( Tetrahedron Letters ; vol. 48; nb. ...

Claims

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Application Information

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IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 刘期凤杨维清张园园黄继红任川洪
Owner XIHUA UNIV
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