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

A kind of acidic ionic liquid catalyzes the method for preparing 1-aryl-2-quinolyl ethanol compound

A technology of acidic ionic liquid and quinoline-based ethanol, which is applied in the field of chemical material preparation, can solve the problems of large usage and complicated purification process, and achieve the effects of less loss, simple and convenient preparation process, and small decline in yield

Active Publication Date: 2020-08-14
马鞍山市泰博化工科技有限公司
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned acidic ionic liquid catalyst is used in a large amount in the reaction (the mole fraction is 20%), and in this method, the purification process for the product is still relatively complicated, and it is necessary to use column chromatography to separate

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
  • A kind of acidic ionic liquid catalyzes the method for preparing 1-aryl-2-quinolyl ethanol compound
  • A kind of acidic ionic liquid catalyzes the method for preparing 1-aryl-2-quinolyl ethanol compound
  • A kind of acidic ionic liquid catalyzes the method for preparing 1-aryl-2-quinolyl ethanol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]1.0mmol m-nitrobenzaldehyde, 1.0mmol 2-methylquinoline and 0.08mmol acidic ionic liquid catalyst were respectively added to a 100ml four-neck flask containing 2ml water with a stirring bar and a condenser tube. Heating and reflux reaction under nitrogen protection for 46min, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, added 1ml of ethyl acetate, crystals were precipitated, filtered with suction, the filter residue was washed with ethyl acetate (2ml×3), and dried in vacuo Obtain 1-(3-nitrophenyl)-2-(quinoline-2-yl) ethanol afterward, and yield is 85%, directly add m-nitrobenzaldehyde and 2- After the methyl quinoline is recycled.

[0035] 1-(3-nitrophenyl)-2-(quinolin-2-yl)ethanol obtained in this example: m.p.154~156°C; 1 H NMR (500MHz, CDCl 3 ): δ=3.23~3.38(m, 2H), 5.31(dd, J=3.0Hz, J=9.9Hz, 1H), 6.46(br, 1H), 7.17(d, J=3.0Hz, 1H), 7.45 (t, J=9.0Hz, 1H), 7.50(t, J=9.0Hz, 1H), 7.64(t, J=9.0Hz, 1H), 7.75(dd...

Embodiment 2

[0038] 1.0mmol of p-nitrobenzaldehyde, 1.0mmol of 2-methylquinoline and 0.08mmol of acidic ionic liquid catalyst were respectively added to a 100ml four-neck flask containing 2ml of water with a stirring bar and a condenser. Heating and reflux reaction under the protection of nitrogen for 43min, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, added 1ml ethyl acetate, crystals precipitated, filtered with suction, the filter residue was washed with ethyl acetate (2ml×3), and dried in vacuo Obtain 1-(4-nitrophenyl)-2-(quinolin-2-yl) ethanol afterward, and yield is 86%, directly adds p-nitrobenzaldehyde and 2- After the methyl quinoline is recycled.

[0039] 1-(4-nitrophenyl)-2-(quinolin-2-yl)ethanol obtained in this example: m.p.151~153°C; 1 H NMR (500MHz, CDCl 3 ): δ=3.25~3.37(m, 2H), 5.42(br, 1H), 6.16(d, J=6.0Hz, 1H), 7.19(d, J=9.1Hz, 1H), 7.58(d, J= 8.6Hz, 1H), 7.61(d, J=9.8Hz, 1H), 7.75(t, J=9.1Hz, 1H), 7.81(d, J=...

Embodiment 3

[0042] 1.0mmol o-nitrobenzaldehyde, 1.0mmol 2-methylquinoline and 0.09mmol acidic ionic liquid catalyst were respectively added to a 100ml four-neck flask containing 2ml water with a stirring bar and a condenser tube. Heating and reflux reaction under nitrogen protection for 57min, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, added 1ml ethyl acetate, crystals precipitated, filtered with suction, the filter residue was washed with ethyl acetate (2ml×3), and dried in vacuo Obtain 1-(2-nitrophenyl)-2-(quinolin-2-yl) ethanol afterward, and yield is 75%, directly add o-nitrobenzaldehyde and 2- After the methyl quinoline is recycled.

[0043] 1-(2-nitrophenyl)-2-(quinolin-2-yl)ethanol obtained in this example: m.p.162~164°C; 1 H NMR (500MHz, CDCl 3 ): δ=3.27(s, 1H), 3.53(d, J=15.0Hz, 1H), 5.76(d, J=9.0Hz, 1H), 6.62(br, 1H), 7.28(d, J=8.1Hz , 1H), 7.39(t, J=8.1Hz, 1H), 7.57(d, J=8.1Hz, 1H), 7.64(t, J=7.5Hz, 1H), 7.79(d,...

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 discloses a method for preparing a 1-aryl-2-quinolyl ethanol compound by catalysis of acidic ionic liquid and belongs to the technical field of chemical material preparation. The methodfor preparing the 1-aryl-2-quinolyl ethanol compound by catalysis of acidic ionic liquid uses aromatic aldehyde and 2-methylquinoline as raw materials to catalytically prepare the 1-aryl-2-quinolyl ethanol compound under the catalysis of the acidic ionic liquid catalyst. The molar amount of the acidic ionic liquid catalyst is 8-13% of the molar amount of the used 2-methylquinoline, and the molar ratio of the aromatic aldehyde to the 2-methylquinoline of the reaction raw materials is 1 to 1. According to the method, the reaction of the aromatic aldehyde and the 2-methylquinoline is catalyzed byselecting the specific acidic ionic liquid as the catalyst to generate the 1-aryl-2-quinolyl ethanol compound. Accordingly, the using amount and the loss amount of the catalyst can be effectively decreased, the method has more catalyst recycling times, and product separation and purification are simple.

Description

technical field [0001] The invention belongs to the technical field of chemical material preparation, and in particular relates to a method for preparing 1-aryl-2-quinolyl ethanol compounds by catalyzing the reaction of aromatic aldehydes and 2-methylquinoline with acidic ionic liquids. Background technique [0002] Quinoline heterocyclic derivatives widely exist in nature as alkaloids, and are a class of organic compounds with important biological and pharmacological activities, which are widely used in the fields of medicinal chemistry and agricultural chemistry. This type of compound has antibacterial, bactericidal, antiallergic, antimalarial, antitumor, anticancer, antihypertensive, antidepressant and memory enhancing effects, and is also used as an inhibitor of HIV virus, as well as a highly efficient catalyst or ligand , also play an important role in the synthesis of chiral molecules. In addition, quinoline heterocyclic derivatives also have important applications in...

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): C07D215/14B01J31/02
CPCY02P20/584
Inventor 卢华沈建忠
Owner 马鞍山市泰博化工科技有限公司
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