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Preparation method of 2-amino-5-iodopyridine

A technology of iodopyridine and amino group is applied in the field of preparation of 2-amino-5-iodopyridine, which can solve the problems of difficulty in obtaining and high cost of raw materials, and achieve the effects of easy realization, high reaction efficiency and high yield.

Pending Publication Date: 2021-12-10
无锡海伦生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Another commonly used synthetic route is to use 2-amino-5-bromopyridine as a raw material. The cost of raw materials is high and difficult to obtain, and organic waste liquid is still generated during synthesis.

Method used

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  • Preparation method of 2-amino-5-iodopyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A preparation method of 2-amino-5-iodopyridine, comprising the following steps:

[0024] Step 1. Put 700g of 2-amino-5-bromopyridine, 80g of cuprous iodide, 1300g of potassium iodide, 80g of N,N-dimethylethylenediamine and 3600ml of DMF into a 10L reaction flask, stir, and replace the nitrogen with vacuum. Raise the temperature, T=100°C and keep it warm for about 5 hours, and the raw material is <5% as detected by HPLC. Cool down to T<40°C, add tap water, stir, and filter;

[0025] Step 2. Wash the filter cake with 5L×3 tap water, and dry it with air blow at 60°C to obtain 600-680g of crude product 1; the filtrate is left to stand for stratification, and the water layer is extracted with 2L×2 toluene, and the organic phases are combined, washed with 3L water, 60 °C and concentrated to dryness under reduced pressure to obtain 250 g of crude product 2;

[0026] Step 3. Dissolve crude product 1 and crude product 2 in 6L of methanol, add 70g of activated carbon, stir at r...

Embodiment 2

[0028] A preparation method of 2-amino-5-iodopyridine, comprising the following steps:

[0029] Put 750g of 2-amino-5-bromopyridine, 82.6g of cuprous iodide, 1440g of potassium iodide, 83g of N,N-dimethylethylenediamine and 3750ml of DMF into a 10L reaction flask, stir, replace nitrogen with vacuum, heat up, T=100 The reaction was incubated at ℃ for about 5 hours, and the raw material was <5% by HPLC. Cool down to T<40°C, add tap water, stir, and filter;

[0030] Step 2. The filter cake was washed with 5L×3 tap water, and dried by blowing at 60°C to obtain 645g of crude product; the filtrate was left standing to separate layers, the water layer was extracted with 2L×2 toluene, the organic phases were combined, washed with 3L of water, and reduced pressure at 60°C Concentrate to dryness to obtain 250 g of crude product;

[0031] Step 3. Dissolve 645g + 250g of crude product in 6L of methanol, add 75g of activated carbon, stir at room temperature, filter, wash the filter resid...

Embodiment 3

[0033] A preparation method of 2-amino-5-iodopyridine, comprising the following steps:

[0034] Step 1. Put 800g of 2-amino-5-bromopyridine, 85g of cuprous iodide, 1500g of potassium iodide, 90g of N,N-dimethylethylenediamine and 3800ml of DMF into a 10L reaction flask, stir, and replace the nitrogen with vacuum. Raise the temperature, T=100°C and keep it warm for about 5 hours, and the raw material is <5% as detected by HPLC. Cool down to T<40°C, add tap water, stir, and filter;

[0035] Step 2. Wash the filter cake with 5L×3 tap water, and dry it with air blow at 60°C to obtain 600-680g of crude product 1; the filtrate is left to separate and separate, the water layer is extracted with 2L×2 toluene, the organic phases are combined, and washed with 3L water, 60 °C and concentrated to dryness under reduced pressure to obtain 250 g of crude product 2;

[0036] Step 3. Dissolve crude product 1 and crude product 2 in 6L of methanol, add 80g of activated carbon, stir at room tem...

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Abstract

The invention relates to a preparation method of 2-amino-5-iodopyridine. The method comprises the following steps: adding 700-800 g of 2-amino-5-bromopyridine, 80-85 g of cuprous iodide, 1300-1500 g of potassium iodide, 80-90 g of N, N-dimethylethylenediamine and 3600-3800 ml of DMF into a 10 L reaction bottle, stirring, carrying out vacuum nitrogen replacement, heating, carrying out heat preservation reaction for about 5 hours when T is equal to 100 DEG C, carrying out HPLC to detect that the raw materials are less than 5%, cooling until T is less than 40 DEG C, adding tap water, stirring, and filtering. According to the invention, the synthesis method has the advantages of efficient and rapid reaction, mild conditions, simple and easily available substrates, wide applicability, short reaction time, high yield and the like, the route design is reasonable, the experimental operation is simple and easy to implement, the yield of the obtained product is high, no organic waste liquid is generated, and the reaction process is safe and pollution-free.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 2-amino-5-iodopyridine. Background technique [0002] 2-Amino-5-iodopyridine, also known as 2-amino-5-iodopyridine, 5-iodo-2-aminopyridine, CAS: 20511-12-0, is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates , Also used in dye production, pesticide production and spices and so on. [0003] The general process is that 2-aminopyridine is synthesized by reaction with iodine in a solvent, and the yield is about 83%. Organic waste liquid is generated during the preparation process, which brings pressure to the environment. Another commonly used synthetic route is to use 2-amino-5-bromopyridine as a raw material, which is expensive and difficult to obtain, and organic waste liquid is still generated during the synthesis. Contents of the invention [0004] (1) Solved technical probl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 梅姜平张永飞陆金华
Owner 无锡海伦生物科技有限公司
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