Synthesis method of 5-methoxy methyl pyridine-2,3-diethyl phthalate

A technology of diethyl diformate and methoxymethyl pyridine is applied in the field of organic chemical synthesis, can solve problems such as low yield, and achieve the effects of simple operation, mild reaction process and improved synthesis yield

Inactive Publication Date: 2016-07-06
CHANGZHOU LANXU CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem mainly solved by the present invention: aiming at the problem that the yield of diethyl 5-methoxymethylpyridine-2,3-dicarboxylate is relatively low and only 50% when it is synthesized by traditional production technology, a 5-methoxymethylpyridine-2 is provided. -methoxymethylpyridine-2, the synthetic method of 3-dicarboxylic acid diethyl ester

Method used

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  • Synthesis method of 5-methoxy methyl pyridine-2,3-diethyl phthalate

Examples

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example 1

[0018] First, add 300 mL of absolute ethanol to a 500 mL three-necked flask equipped with a thermometer and a reflux device, and then add 10 mL of 98% concentrated sulfuric acid at a rate of 2 mL / min at a stirring speed of 600 r / min. , after the temperature of the solution in the there-necked flask is naturally cooled to room temperature, then add 1.80g of 5-picoline-2,3-dicarboxylic acid in the there-necked flask, then heat the three-necked flask with an oil bath, so that the temperature of the solution in the there-necked flask is controlled at 110°C, keep warm for 1 hour, track the reaction by thin-layer chromatography, until the solution does not contain 5-picoline-2,3-dicarboxylic acid, the reaction ends, and 5-picoline-2,3-dicarboxylic acid dicarboxylate is obtained Ethyl ester solution; add 1.8g N-bromosuccinimide to the above solution, react for 1h, track the reaction by thin-layer chromatography, until the reaction solution no longer contains 5-picoline-2,3-dicarboxyli...

example 2

[0021] First, add 330 mL of absolute ethanol to a 500 mL three-necked flask equipped with a thermometer and a reflux device, and then add 13 mL of 98% concentrated sulfuric acid at a rate of 2 mL / min at a stirring speed of 700 r / min. , the temperature of the solution in the there-necked flask is naturally cooled to room temperature, then add 1.90g of 5-picoline-2,3-dicarboxylic acid in the there-necked flask, then heat the three-necked flask with an oil bath, so that the temperature of the solution in the there-necked flask is controlled at 120°C, keep warm for 1.5h, track the reaction by thin layer chromatography until the solution does not contain 5-methylpyridine-2,3-dicarboxylic acid, the reaction is over, and 5-methylpyridine-2,3-dicarboxylic acid is obtained Diethyl ester solution; add 1.9g N-bromosuccinimide to the above solution, react for 1.5h, track the reaction by thin-layer chromatography until the reaction solution no longer contains 5-picoline-2,3-di Diethyl form...

example 3

[0024] First, add 350 mL of absolute ethanol to a 500 mL three-necked flask equipped with a thermometer and a reflux device, and then add 15 mL of 98% concentrated sulfuric acid at a rate of 2 mL / min at a stirring speed of 800 r / min. , after the temperature of the solution in the there-necked flask is naturally cooled to room temperature, then add 2.00g of 5-methylpyridine-2,3-dicarboxylic acid in the there-necked flask, then heat the three-necked flask with an oil bath, so that the temperature of the solution in the there-necked flask is controlled at 130°C, keep warm for 2 hours, track the reaction by thin-layer chromatography until the solution does not contain 5-methylpyridine-2,3-dicarboxylic acid, and the reaction is completed to obtain 5-methylpyridine-2,3-dicarboxylic acid Ethyl ester solution; add 2.0g N-bromosuccinimide to the above solution, react for 2h, track the reaction by thin-layer chromatography until the reaction solution no longer contains 5-picoline-2,3-dic...

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Abstract

The invention discloses a method for synthesizing diethyl 5-methoxymethylpyridine-2,3-dicarboxylate, and belongs to the technical field of organic chemical synthesis. The present invention uses 5-picoline-2,3-dicarboxylic acid as raw material, firstly 5-picoline-2,3-dicarboxylic acid and absolute ethanol generate 5-picoline-2,3-dicarboxylic acid diethyl ester, then N-bromosuccinimide was added to further generate 5-bromomethylpyridine-2,3-diethyl dicarboxylate, and then to 5-bromomethylpyridine-2,3-diethyl ester Triethylamine and methanol are added dropwise to diethyl formate to carry out a nucleophilic substitution reaction, and after the reaction, a solution of 5-methoxymethylpyridine-2,3-diethyl dicarboxylate is obtained. After pressure distillation, a kind of 5-methoxymethylpyridine-2,3-diethyl dicarboxylate of the present invention is obtained. The invention is not only simple and easy to operate, but also the synthesis yield is significantly improved, up to 91%.

Description

technical field [0001] The invention discloses a method for synthesizing diethyl 5-methoxymethylpyridine-2,3-dicarboxylate, which belongs to the technical field of organic chemical synthesis. Background technique [0002] Diethyl 5-methoxymethylpyridine-2,3-dicarboxylate is an intermediate for the synthesis of imazethapyr. According to relevant literature reports, there are currently three production processes for this product. The first one is based on Ethyl chloroacetate reacts with diethyl oxalate, and then reacts with 2-methacrolein. The second is obtained by condensation of diethyl aminomaleate and 2-methoxymethacrolein. Three are obtained by oxidative ring opening of 3-methoxymethyl-8-carboxyquinoline. [0003] The first process route is too long, and the total yield is low, so it is not suitable for industrialized production. Although the second kind has mild reaction conditions and short route, the 5-methoxymethylpyridine-2,3-dicarboxylic acid diethyl ester obtaine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/803
CPCC07D213/803
Inventor 汪巍孟浩影
Owner CHANGZHOU LANXU CHEM CO LTD
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