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

Synthetic method of tetralin amines compounds

A tetrahydronaphthylamine and synthetic method technology, applied in the direction of organic chemistry, etc., can solve the problems of harsh experimental conditions, environmental pollution, etc., achieve the effects of reducing the elimination of three industrial wastes, avoiding the use of organic solvents, and low production costs

Active Publication Date: 2009-03-11
SHANGHAI CHEMPARTNER CO LTD
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is in order to overcome the harsh experimental conditions and serious environmental pollution defects of the synthetic method of existing tetrahydronaphthylamine compounds, and provide a product with high yield and purity, easy and convenient operation, Low cost, environmentally friendly, easy to the synthetic method of industrialized tetrahydronaphthylamine compounds

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
  • Synthetic method of tetralin amines compounds
  • Synthetic method of tetralin amines compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] In a three-necked reaction flask equipped with a thermometer and a stirrer, add 1-nitronaphthalene (8.7 g, 0.05 mol), water (100 mL), 1:1 (W / W) Ni- Al alloy (4.35g), then heated to 60°C with stirring. Then 1 wt% aqueous sodium hydroxide solution (100 ml) was added dropwise for 1 hour. The reaction was directly followed by TLC to complete the reaction of 1-nitronaphthalene (5h). After the reaction, the reaction solution was cooled to room temperature (20-25° C.), left to filter, extracted the aqueous phase with dichloromethane organic solvent, concentrated and evaporated the organic solvent to obtain 1-tetrahydronaphthylamine with a yield of 76% and a purity of 98.2 % (HPLC).

Embodiment 2

[0018] In a three-necked reaction flask equipped with a thermometer and a stirrer, add 2-nitronaphthalene (8.7 g, 0.05 mol), water (80 mL), 1:1 (W / W) Ni- Al alloy (8.7g), then stirred and heated to 85°C. Then 20wt% cesium hydroxide aqueous solution (80ml) was added dropwise for 1 hour. The reaction was directly followed by TLC to complete the reaction of 1-nitronaphthalene (4h). After the reaction, the reaction liquid was cooled to room temperature, stood and filtered, extracted the aqueous phase with dichloromethane organic solvent, concentrated and evaporated the organic solvent to obtain 2-tetrahydronaphthylamine with a yield of 80% and a purity of 98.8% (HPLC).

Embodiment 3

[0020] In a three-necked reaction flask equipped with a thermometer and a stirrer, add 1-nitronaphthalene (8.7g, 0.05mol), water (500mL), 1:1 (W / W) Ni -Al alloy (43.5g), then stirred and heated to 50°C. Then 10wt% lithium hydroxide aqueous solution (500ml) was added dropwise for 1 hour. The reaction was directly followed by TLC to complete the reaction of 1-nitronaphthalene (3h). After the reaction, the reaction solution was cooled to room temperature (20-25° C.), left to filter, extracted the aqueous phase with dichloromethane organic solvent, concentrated and evaporated the organic solvent to obtain 1-tetrahydronaphthylamine with a yield of 86% and a purity of 99.2 %(HPLC)

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 synthesizing a tetranap amine compound as shown in formula II, which comprises the following steps: nitronaphthalene compound as shown in formula I reacts with Ni-Al alloy in alkaline aqueous solution, wherein X and Y are selected from H, F, Cl, Br or I respectively. The method adopts water as a reaction medium so as to avoid the use of toxic and harmful organic solvent, reduce exhaust of industrial three wastes and be friendly to the environment, has the advantages of higher product yield and purity, simple operation and low production cost, is not only applicable to small-scale preparation for a laboratory, but also applicable to large-scale industrialized production.

Description

technical field [0001] The present invention relates to a kind of synthesis method of compound, in particular to a kind of synthesis method of tetrahydronaphthylamine compound. Background technique [0002] Tetrahydronaphthylamine compounds are very important chemical intermediates, especially in the industries of medicine, pesticides, dyes and cosmetics, which have a very wide range of uses. [0003] At present, the synthesis method of tetralamine compounds is mainly carried out by reaction at low temperature in liquid ammonia medium or by high-pressure reduction. [0004] R.A. Benkeser (US 4533752) et al. reported that taking naphthylamine as a raw material to prepare tetrahydronaphthylamine through metal calcium reduction. The main disadvantages of this method are: the reaction needs to use dangerous metal calcium as a reducing agent, ethylenediamine, which is toxic and harmful to the environment and workers, is used as a solvent, the post-treatment of the reaction waste...

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): C07C211/58C07C211/59
Inventor 刘国斌李原强刘军
Owner SHANGHAI CHEMPARTNER CO LTD
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