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

Semi-sandwich ruthenium complex and its preparation method, preparation method of ligand and reduction method of nitrobenzene compounds

A technology for aniline compounds and nitrobenzenes, which is applied in the field of semi-sandwich ruthenium complexes and their preparation, and the reduction of nitrobenzene compounds, can solve the problems of troublesome product separation, environmental pollution, and high production costs

Active Publication Date: 2019-03-26
ANHUI NORMAL UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the most commonly used preparation method of aniline compounds is the iron powder reduction method, because of the disadvantages of high equipment requirements, environmental pollution, large energy consumption, troublesome product separation, etc. in the production process, another preparation method is the catalytic hydrogenation method, The main disadvantage of this method is that the reaction requires higher pressure and the production cost is higher

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
  • Semi-sandwich ruthenium complex and its preparation method, preparation method of ligand and reduction method of nitrobenzene compounds
  • Semi-sandwich ruthenium complex and its preparation method, preparation method of ligand and reduction method of nitrobenzene compounds
  • Semi-sandwich ruthenium complex and its preparation method, preparation method of ligand and reduction method of nitrobenzene compounds

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0029] In the preparation method of above-mentioned semi-sandwich ruthenium complex, the consumption of each material can be selected in wide range, but in order to further improve the productive rate of product, preferably, relative to the compound of structure shown in formula (C) of 1mmol , the amount of 2-oxazolinylphenol ligand with the structure shown in formula (B) is 1-3mmol, the amount of strong base and weak acid salt is 1-3mmol, and the amount of organic solvent is 5-25mL.

[0030] Simultaneously, in the preparation method of above-mentioned semi-sandwich ruthenium complex, the specific kind of basic compound also can be selected in wide range, but in order to further improve the productive rate of reaction rate and product, preferably, basic compound is alkali and / or Or strong base and weak acid salt; more preferably, the basic compound is selected from one or more of sodium acetate, potassium acetate, potassium carbonate, sodium carbonate and sodium hydroxide.

[...

Embodiment 1

[0049] Preparation of:

[0050] Add ethyl salicylate (4.4mL, 30mmol) and 2-amino-2-methyl-1-propanol (2.39mL, 30mmol) mixture into a 100mL round bottom flask, heat to 170°C and reflux for 10h, then cool to room temperature Finally, use a rotary evaporator to spin dry, load the crude reaction mixture on a silica gel column, pass through the column with ethyl acetate and n-hexane to obtain a white oily intermediate product, add the product to a 50mL reaction tube, add 10mL dichloromethane and 0.5 mL of thionyl chloride was reacted in an ice-water bath for 2 days, filtered with suction and washed with water and dichloromethane to obtain 2.97 g of a white solid with a yield of 56%.

[0051] The obtained characterization data results: 1 H NMR (300MHz, CDCl 3 )δ12.16(s,1H),7.39(s,1H),7.37(s,1H),6.97(d,J=9.0Hz,1H),6.84(t,1H),4.56(s,1H), 3.80(m,1H),3.67(m,1H),1.38(d,J=9.0Hz,3H); 13 C NMR (125MHz, CDCl3) δ170.68, 161.65, 134.65, 126.34, 119.24, 118.78, 114.65, 43.13, 37.70, 32.24...

Embodiment 2

[0053] Preparation of:

[0054] According to the method of Example 1, 2.46 g of white liquid was obtained, and the yield was 43%. The difference is that 2-amino-2-methyl-1-propanol is replaced by 2-amino-1-butanol, and the reflux time is changed to 8h.

[0055] The obtained characterization data results: 1 H NMR (300MHz, CDCl 3 )δ12.17(s,1H),7.40(t,2H),6.99(d,J=9.0Hz,1H),6.85(t,1H),4.35(t,1H),3.78(m,2H), 1.75(m,2H),1.00(t,3H);IR(KBr,cm -1 ):3081(s), 2968(m), 1626(vs), 1546(vs), 1494(s), 1454(s), 1372(s), 1303(s), 1240(s), 1156(m ),1099(s),1041(m),980(m),888(m),755(s),688(s),653(w),593(m).

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 half-sandwich ruthenium complex and a preparation method thereof, a preparation method of ligand and a reduction method of a nitrobenzene compound. The structure of the half-sandwich ruthenium complex is shown by formula (A), wherein in the formula (A), R1 and R2 are separately selected from H or C1-C7 alkyl, and X is halogen; preferentially, the C1-C7 alkyl is methyl, ethyl or phenyl, and X is chlorine; more preferentially, R1 is H, R2 is H or C1-C7 hydrocarbyl, and X is chlorine; and most preferentially, R1 is H, R2 is methyl, ethyl or phenyl, and X is chlorine. The half-sandwich ruthenium complex is prepared by an efficient preparation method; the half-sandwich ruthenium complex can efficiently and mildly catalyze a nitrobenzene compound to reduce the nitrobenzene compound into an aniline compound; and moreover, the conditions of the preparation method of ligand in the half-sandwich ruthenium complex are relatively mild, and the yield is relatively high.

Description

technical field [0001] The invention relates to a ruthenium complex, in particular to a semi-sandwich ruthenium complex, a preparation method thereof, a ligand preparation method and a reduction method of nitrobenzene compounds. Background technique [0002] The complexes of ruthenium with a semi-sandwich structure have unique chemical stability, excellent optical properties and rich redox properties. A very active field. Coordination compounds of ruthenium with a half-sandwich structure play an important role in photochemistry, organic catalysis, olefin metathesis, electrochemistry, fluorescent ion probes, and gas sensing. Therefore, it is a very important research content to synthesize and explore the application of a series of complexes with semi-sandwich structure ruthenium; but there are still some defects in the existing preparation methods of complexes with semi-sandwich structure ruthenium, such as: longer reaction time, Lower yield etc. [0003] Aniline compound ...

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): C07F15/00B01J31/22C07C209/36C07C211/52C07C211/47C07C233/65C07C231/12C07B43/04
CPCB01J31/2217B01J31/2295B01J2231/641B01J2531/0241B01J2531/821C07B43/04C07C209/36C07C231/12C07F15/0046C07C211/52C07C211/47C07C233/65
Inventor 贾卫国凌硕孙影
Owner ANHUI NORMAL UNIV
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