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Method for preparing 1-(3-methoxypyridine-2-yl)-2-acetone

A technology of methoxypyridine and acetone, which is applied in the field of preparation of a new broad-spectrum anticoccidial drug hemosanone intermediate, can solve the problems of harsh reaction conditions, low yield, and inability to realize industrialization, and achieve production cost control, The effect of improving the overall yield and easy control of reaction conditions

Active Publication Date: 2021-01-29
ZHEJIANG GENEBEST PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, in the domestic market, there is no mature preparation process of peroxide, and most of the supply depends on imports. The key intermediate 1-(3-methoxypyridin-2-yl)-2-propanone is due to the harsh reaction conditions. , the yield is low and industrialization cannot be realized, thus affecting the overall process improvement of peroxide

Method used

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  • Method for preparing 1-(3-methoxypyridine-2-yl)-2-acetone
  • Method for preparing 1-(3-methoxypyridine-2-yl)-2-acetone

Examples

Experimental program
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Effect test

Embodiment 1

[0019] A. Preparation of ((3-methoxypyridin-2-yl)methyl)magnesium chloride (Ⅱ)

[0020] Add 2-methyl-3-methoxypyridine (123g, 1.0mol), 10% isopropylmagnesium chloride in 2-methylfuran solution (1125g, about 1.1mol) into a reactor with a stirring and heating device ). After stirring evenly, add lithium chloride (42.5g, 1.0mol) in batches, heat to reflux for 10 hours after the addition, and cool to room temperature after the reaction to obtain ((3-methoxypyridin-2-yl)methanol Base) Magnesium chloride (II) in 2-methyltetrahydrofuran solution, without further separation and purification, can be directly used in the next reaction.

[0021] B. Preparation of 1-(3-methoxypyridin-2-yl)-2-propanone (I)

[0022] Add the Grignard reagent prepared in the previous steps (calculated as 1 times of 2-methyl-3-methoxypyridine) into the reactor, stir evenly and cool to -5-5°C, add acetic anhydride in batches ( 710g), keep the temperature of the reaction mixture not exceeding 10°C during th...

Embodiment 2

[0026] A. Preparation of ((3-methoxypyridin-2-yl)methyl)magnesium chloride (Ⅱ)

[0027] Add 2-methyl-3-methoxypyridine (123g, 1.0mol), 10% isopropylmagnesium chloride in 2-methylfuran solution (1025g, about 1.0mol ). After stirring evenly, add lithium chloride (42.5g, 1.0mol) in batches, heat to reflux state and react for 6 hours after the addition, and cool to room temperature after the reaction to obtain ((3-methoxypyridin-2-yl)methanol Base) Magnesium chloride (II) in 2-methyltetrahydrofuran solution, without further separation and purification, can be directly used in the next reaction.

[0028] B. Preparation of 1-(3-methoxypyridin-2-yl)-2-propanone (I)

[0029] Add the Grignard reagent prepared in the previous steps (calculated as 1 times of 2-methyl-3-methoxypyridine) into the reactor, stir evenly and cool to -5-5°C, add acetic anhydride in batches ( 310g), the temperature of the reaction mixture should not exceed 10°C during the addition process. After the additio...

Embodiment 3

[0033] A. Preparation of ((3-methoxypyridin-2-yl)methyl)magnesium chloride (Ⅱ)

[0034] Add 2-methyl-3-methoxypyridine (123g, 1.0mol), 10% isopropylmagnesium chloride in 2-methylfuran solution (1076g, about 1.05mol ). After stirring evenly, add lithium chloride (42.5g, 1.0mol) in batches, heat to reflux state and react for 8 hours after the addition, and cool to room temperature after the reaction to obtain ((3-methoxypyridin-2-yl)methanol Base) Magnesium chloride (II) in 2-methyltetrahydrofuran solution, without further separation and purification, can be directly used in the next reaction.

[0035] B. Preparation of 1-(3-methoxypyridin-2-yl)-2-propanone (I)

[0036] Add the Grignard reagent prepared in the previous steps (calculated as 1 times of 2-methyl-3-methoxypyridine) into the reactor, stir evenly and cool to -5-5°C, add acetic anhydride in batches ( 510g), keep the temperature of the reaction mixture not exceeding 10°C during the addition process, continue to kee...

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Abstract

The invention discloses a novel preparation method of a common novel broad-spectrum anticoccidial drug halofuginone intermediate, and relates to a specific preparation method of a compound 1-(3-methoxypyridine-2-yl)-2-acetone. The method sequentially comprises the following steps of: by taking 2-methyl-3-methoxy pyridine as a raw material, performing exchange to obtain a corresponding Grignard reagent; making the Grignard reagent react with acetic anhydride to form a seven-membered ring intermediate product; and finally hydrolyzing the seven-membered ring intermediate product to obtain the product. The invention provides a brand-new synthetic route; the used raw materials are mature in process, sufficient in market supply and wide in source; the reaction conditions of each step are mild, and the process is simple. The method can be applied to large-scale production.

Description

technical field [0001] The invention relates to a preparation method of a novel broad-spectrum anticoccidial drug hemosanone intermediate, in particular to a method for preparing the compound 1-(3-methoxypyridin-2-yl)-2-acetone. Background technique [0002] In the field of animal husbandry, livestock and poultry are susceptible to a series of diseases caused by coccidia infection during the growth process, which affects yield and quality. In recent years, the investment in diseases caused by parasitic infection and their treatment in the global animal husbandry It has been greatly improved in the past, and spectral anticoccidiostats are also widely used in animal husbandry. As a broad-spectrum antiparasitic drug, Changshanone is effective against chicken tenderness, poisoning, heap type, displacement, giant, and Eimeria brucei It is effective against coccidian sporozoites, first-generation and second-generation schizonts. [0003] At present, in the domestic market, there ...

Claims

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Application Information

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IPC IPC(8): C07D213/65
CPCC07D213/65
Inventor 宋崎杰冯忠平蒋健蒋沈潇
Owner ZHEJIANG GENEBEST PHARMA