Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for preparing 2,3-pyridinedicarboxylate compounds

A technology of dicarboxylic acid esters and compounds, applied in the field of organic synthesis, can solve the problems of low yield, many by-products, unfavorable purification of intermediates, etc., and achieve the effects of easy availability of raw materials and simple operation

Active Publication Date: 2015-06-10
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
View PDF7 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

U.S. Patent US 5281713 discloses the use of quinoline or quinoline derivatives to oxidize and then carry out esterification to obtain 2,3-dicarboxylate compounds, but the yield of this method is low, preferably less than 50%, if necessary High-purity products also need to be purified; EP 0461401A1 discloses the use of butenedioic acid halogenated derivatives and acrolein compounds to condense dicarboxylic acid ester compounds in the presence of ammonia or ammonia salts, but the products synthesized by this method There are many by-products, and the compound can only be characterized by melting point; Japanese Patent JP1-143857 discloses the method of condensing 2-enaminosuccinate and acrolein compound to synthesize 2,3-dicarboxylate compound, but It is not conducive to the purification of intermediates due to many by-products

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing 2,3-pyridinedicarboxylate compounds
  • Method for preparing 2,3-pyridinedicarboxylate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 3.60g of palladium iodide into a 250mL three-necked flask, add 70mL of acetic acid, add 7.6g of formic acid dropwise under stirring, add 16.5g of 1-benzyl-2,3-dicarboxylic acid ethyl ester-5-methyl-4-hydrogen -pyridine, the reaction mixture was stirred at 80°C for 9 hours, cooled to room temperature, filtered to recover the solid, and the filtrate was distilled under reduced pressure to recover acetic acid to obtain 11.1 g of the product, with a yield of 91.8%.

Embodiment 2

[0020] Add 2.30g of palladium nitrate into a 250mL three-necked flask, add 70mL of acetic acid, add 8.1g of formic acid dropwise under stirring, add 22.8g of 1-benzyl-2,3-dicarboxylic acid ethyl ester-5-methyl-4-hydrogen- Pyridine, the reaction mixture was stirred at 100°C for 6 hours, cooled to room temperature, filtered to recover the solid, and the filtrate was distilled under reduced pressure to recover acetic acid to obtain 14.8 g of the product, with a yield of 87.9%.

Embodiment 3

[0022] Add 2.66g of palladium bromide into a 250mL three-necked flask, add 70mL of acetic acid, add 8.3g of formic acid dropwise under stirring, add 22.8g of 1-benzyl-2,3-dicarboxylic acid ethyl ester-5-methyl-4-hydrogen -pyridine, the reaction mixture was stirred at 80°C for 7 hours, cooled to room temperature, filtered to recover the solid, and the filtrate was distilled under reduced pressure to recover acetic acid to obtain 14.4g of the product, with a yield of 86.7%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

A disclosed method for preparing 2,3-pyridinedicarboxylate compounds is shown as the first reaction equation shown in the specification, a compound 1 is reacted with a palladium salt in a formic acid / acetic acid system for preparing 2,3-pyridinedicarboxylate. The specific operation comprises: dispersing the palladium salt in acetic acid, dropwise adding formic acid and adding the compound 1, heating to 50-120 DEG C, then heating for 2-15 h at the temperature, stopping heating, cooling the reaction materials to room temperature, filtering out generated palladium, performing reduced-pressure distillation on the filtrate to recover acetic acid and obtain the corresponding 2,3-pyridinedicarboxylate, wherein the molar ratio of the palladium salt to the compound 1 is 0.005-0.3:1, and the molar ratio of formic acid to the compound 1 is 1.1-5:1. The experiment is simple, the raw materials are easily available, and the preparation method is an environment-friendly preparation method for preparing 2,3-pyridinedicarboxylate with high purity and high yield. In the reaction equation, R1 is selected from H, CH3 or CH2-O-CH3, R2 and R3 can be same or different and are selected from CH3 or CH2-CH3.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for preparing 2,3-dicarboxylate pyridine compounds. technical background [0002] 2,3-dicarboxylate pyridine compounds are key intermediates of imidazolinone herbicides. U.S. Patent US 5281713 discloses the use of quinoline or quinoline derivatives to oxidize and then carry out esterification to obtain 2,3-dicarboxylate compounds, but the yield of this method is low, preferably less than 50%, if necessary High-purity products also need to be purified; EP 0461401A1 discloses the use of butenedioic acid halogenated derivatives and acrolein compounds to condense dicarboxylic acid ester compounds in the presence of ammonia or ammonia salts, but the products synthesized by this method There are many by-products, and the compound can only be characterized by melting point; Japanese Patent JP1-143857 discloses the method of condensing 2-enaminosuccinate and acrolein compound t...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/803C07D213/80
CPCC07D213/80C07D213/803
Inventor 姜鹏
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD