Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of indacaterol intermediate diethylbenzene

A technology for o-diethylbenzene and o-ethylacetophenone, which is applied in the field of preparing o-diethylbenzene and can solve problems such as large environmental pollution

Inactive Publication Date: 2014-07-02
TIANJIN INSTITUTE OF PHARMA RESEARCH
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Journal of the American Chemical Society, 1949, vol.71, p.1362-1366, using o-ethyl acetophenone as raw material, using Zn-Hg / HCl for reduction, causing great environmental pollution

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
  • Preparation method of indacaterol intermediate diethylbenzene
  • Preparation method of indacaterol intermediate diethylbenzene
  • Preparation method of indacaterol intermediate diethylbenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] o-Ethylacetophenone (29.6g, 0.20mol), 80% hydrazine hydrate (97.7ml, 1.6mol) and absolute ethanol (400ml) were mixed, magnetically stirred, and refluxed at 25°C for 2-6 hours. After the reaction, add appropriate amount of distilled water, extract with ethyl acetate, wash with saturated brine, anhydrous Na 2 SO 4 Drying and rotary evaporation gave white crystal II (28.9 g, yield 89.1%). 1H-NMR (CDCl3) δ7.24(d, 2H), 7.16(t, 2H), 5.44(s, 2H), 2.68(m, 2H), 2.15(s, 3H), 1.23(t, 3H).

Embodiment 2

[0024] o-Ethylacetophenone (45.00g, 0.30mol), 80% hydrazine hydrate (18.3ml, 0.30mol) and absolute ethanol (700ml) were mixed, stirred by magnetic force, and reacted at 25°C for 8 hours. After the reaction, add appropriate amount of distilled water, extract with ethyl acetate, wash with saturated brine, anhydrous Na 2 SO 4 Drying and rotary evaporation gave white crystal II (40.1 g, yield 82.4%).

Embodiment 3

[0026] o-Ethylacetophenone (29.6g, 0.20mol), 80% hydrazine hydrate (244ml, 4mol) and absolute ethanol (400ml) were mixed, stirred by magnetic force, and reacted at 100°C for 3 hours. After the reaction, add appropriate amount of distilled water, extract with ethyl acetate, wash with saturated brine, anhydrous Na 2 SO 4 Drying and rotary evaporation gave white crystal II (27.7 g, yield 85.4%).

[0027] Compound formula (I)

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 provides a preparation method of an intermediate diethylbenzene. The preparation method comprises the steps: reacting diethyl acetophenone and hydrazine hydrate, and making a compound react with alkaline to obtain the diethylbenzene. The preparation method provided by the invention has the advantages of availability of raw materials, simplicity and convenience in operation, good quality, high yield and low cost, and is suitable for large-scale industrialized production.

Description

technical field [0001] The present invention relates to a new method for preparing o-diethylbenzene. Background technique [0002] Indacaterol, chemical name is (R)-5-[2-(5,6-diethylindan-2-amino)-1-hydroxyethyl]-8-hydroxy-1H-quinoline-2 -Ketomaleate, a new type of ultra-long-acting beta 2 Receptor agonist is a new inhaled drug for chronic obstructive pulmonary disease (COPD), with rapid onset and long-lasting bronchodilation effect. It only needs to be taken once a day to significantly improve the patient's lung function and wheezing symptoms, and is safe. and well tolerated, it was first approved for marketing in the European Union in November 2009. [0003] [0004] O-diethylbenzene is one of the important intermediates, and its structure is shown in formula (I): [0005] [0006] In the prior art, Journal of the American Chemical Society, 1992, vol.114(8), p.3123-3125 describes the synthesis method of (I), using 1,2-divinylbenzene hydrogenation, the yield is onl...

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
IPC IPC(8): C07C15/02C07C1/32
Inventor 李树军闫少杰韩李梅黄汉忠
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com