Check patentability & draft patents in minutes with Patsnap Eureka AI!

Method for preparing functionalized methyl 2-(3-oxoisoindoline-1-subunit) acetate from carbon dioxide

A technology of oxoisoindoline and functionalization, which is applied in the field of synthesizing methyl 2-acetate, and achieves the effects of high yield, easy separation and purification, and wide source of raw materials

Pending Publication Date: 2022-05-17
CHANGZHOU UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the relationship between o-alkynyl amides and CO 2 The reaction has not yet been reported

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 functionalized methyl 2-(3-oxoisoindoline-1-subunit) acetate from carbon dioxide
  • Method for preparing functionalized methyl 2-(3-oxoisoindoline-1-subunit) acetate from carbon dioxide
  • Method for preparing functionalized methyl 2-(3-oxoisoindoline-1-subunit) acetate from carbon dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: (E)-2-(2-benzyl-3-oxoisoindoline-1-methylene)-2-acetic acid methyl ester

[0027] Methyl(E)-2-(2-benzyl-3-oxoisoindolin-1-ylidene)-2-phenylacetate

[0028]

[0029] N-benzyl-2-(phenylethynyl)benzamide (0.2mmol, 62.23mg), K 2 CO 3 (0.6 mmol, 82.93 mg) and DMF (2.0 mL) were added to a 20 mL Schlenk tube fitted with a Teflon cap. The reaction vessel was evacuated to about -0.1MPa (each last 30 seconds) and backfilled with CO three times 2 (1 atmosphere). Then, the Schlenk tube was reacted in a 60°C oil bath for 12 hours. After that, MeI (0.8 mmol) was added to the reaction mixture, the reaction mixture was stirred at 50 °C for about 1 hour, then the reaction mixture was diluted with brine and extracted (EA) with ethyl acetate at least 6 times (2 mL×6). Subsequently, the combined organic layers were washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The residue was purified by flash chromatography on silica gel (PE / EA 10 / 1) to ...

Embodiment 2

[0030] Example 2: (E)-2-(2-methyl-3-oxoisoindoline-1-ethylene)-2-acetic acid methyl ester

[0031] Methyl(E)-2-(2-methyl-3-oxoisoindolin-1-ylidene)-2-phenylacetate

[0032]

[0033] N-methyl-2-(phenylethynyl)benzamide (0.2mmol, 47.02mg), K 2 CO 3 (0.6 mmol, 82.93 mg) and DMF (2.0 mL) were added to a 20 mL Schlenk tube fitted with a Teflon cap. The reaction vessel was evacuated to about -0.1MPa (each last 30 seconds) and backfilled with CO three times 2 (1 atmosphere). Then, the Schlenk tube was reacted in a 60°C oil bath for 12 hours. After that, MeI (0.8 mmol) was added to the reaction mixture, the reaction mixture was stirred at 50 °C for about 1 hour, then the reaction mixture was diluted with brine and extracted (EA) with ethyl acetate at least 6 times (2 mL×6). Subsequently, the combined organic layers were washed with anhydrous Na 2 SO 4Dry and concentrate under reduced pressure. The residue was purified by flash chromatography on silica gel (PE / EA 10 / 1) to gi...

Embodiment 3

[0034] Example 3: (E)-2-(2-isopropyl-3-oxoisoindoline-1-methylene)-2-acetic acid methyl ester Methyl(E)-2-(2-isopropyl- 3-oxoisoindolin-1-ylidene)-2-phenylacetate

[0035]

[0036] N-isopropyl-2-(phenylethynyl)benzamide (0.2mmol, 52.63mg), K 2 CO 3 (0.6 mmol, 82.93 mg) and DMF (2.0 mL) were added to a 20 mL Schlenk tube fitted with a Teflon cap. Vacuumize the reaction vessel to about -0.1Mpa (the last 30 seconds each time) and backfill CO three times 2 (1 atmosphere). Then, the Schlenk tube was reacted in a 60°C oil bath for 12 hours. After that, MeI (0.8 mmol) was added to the reaction mixture, the reaction mixture was stirred at 50°C for about 1 hour, then the reaction mixture was diluted with brine and extracted (EA) with ethyl acetate at least 6 times (2 mL×6). Subsequently, the combined organic layers were washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The residue was purified by flash chromatography on silica gel (PE / EA 10 / 1) to gi...

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

The invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a method for preparing functionalized 2-(3-oxoisoindoline-1-subunit) methyl acetate from carbon dioxide. The method comprises the following steps: by taking o-alkynyl amide and carbon dioxide as raw materials and N, N-dimethylformamide as a solvent, reacting in an oil bath pan at 60 DEG C for 12 hours under the promotion of alkali, and then adding methyl iodide to continuously react for 1 hour to obtain a product. And a series of functionalized 2-(3-oxoisoindoline-1-subunit) methyl acetate compounds with high yield can be obtained by simply post-treating the reaction product. The o-alkynyl amides containing different substituent groups can be used as reaction substrates to obtain the corresponding 2-(3-oxoisoindoline-1-subunit) methyl acetate compound.

Description

technical field [0001] The invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a simple and efficient synthesis of 2-(3 -Oxoisoindoline-1-ylidene) methyl acetate method. Background technique [0002] Methyl 2-(3-oxoisoindoline-1-ylidene)acetate is an important intermediate in organic synthesis, and its derivatized products have good pharmacological activity and can be used as antiarrhythmic drugs, prevention and Treatment of infarction, angina pectoris, etc., therefore, the effective synthesis of this type of compound has strong application value. (See: Chen, X.; Zhao, S.; Li, H.; Wang, X.; Geng, A.; Cui, H.; Lu, T.; Chen, Y.; Zhu, Y.; Design, synthesis and biological evaluation of novel isoindolinone derivatives as potent histone deacetylase inhibitors, Eur. J. Med. Chem. 2019, 168, 110-122.). [0003] In the existing reports, the synthesis method of this type of compound is mainly obtained by utilizing the ...

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 Applications(China)
IPC IPC(8): C07D209/46C07D409/06C07D495/04
CPCC07D209/46C07D409/06C07D495/04
Inventor 孙松沙宇柏君雪李渺
Owner CHANGZHOU UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com