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

Preparation method of isoquinoline phosphite ester compound

A technology of isoquinoline phosphite and compounds, which is applied in the direction of phosphorus organic compounds, can solve the problems that are not conducive to the promotion and popularization of industrialization, the production rate is not very high, and the production cost is increased, so as to achieve high utilization rate of atom economy and low production cost. Low, productivity-enhancing effect

Inactive Publication Date: 2018-11-06
WENZHOU UNIVERSITY
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Though said method can make isoquinoline phosphite compound, yet this method needs more expensive metal catalyst Pd(MeCN) 2 Cl 2 , thereby greatly increasing production costs
In addition, the yield of this method is not very high, and there are many types of compounds added, so the use of the above preparation method is not conducive to the popularization of industrialization

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 isoquinoline phosphite ester compound
  • Preparation method of isoquinoline phosphite ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 32.0 mg (0.1 mmol) Tert-butoxycarbonyl (3-phenyl isoquinolinium-2-yl) amide (R1 = hydrogen, R2 = phenyl, R3 = tert-butyryl, R4 = ethyl), 27.6 mg (0.2 mmol) Diethyl phosphate, 27.6 mg (0.2 mmol) K 2 CO 3 , 1.9 mg (0.01 mmol) CuI was added to the reaction test tube, and then 2 mL of DCE (1,2 dichloroethane) was added, at 120 o The crude product was obtained by heating and reacting at C for 24 hours, cooled after the reaction, filtered, the filtrate was rotary evaporated, and the solvent was removed. The residue was subjected to silica gel column chromatography, washed with petroleum ether, and detected by TLC. The solvent was distilled off, and dried in vacuo to obtain 28.0 mg of diethyl (3-phenylisoquinolin-1-yl) phosphonate as a light yellow liquid, with a yield of 82%. 1 H NMR (500 MHz, CDCl 3 ) δ: 8.92 (d, J = 8.5 Hz,1H), 8.15(m, 3H), 7.86 (d, J = 8.0 Hz,1H), 7.64 (dt, J = 15.0, 7.3 Hz, 2H), 7.49 (t, J = 7.5 Hz,2H), 7.40 (t, J = 7.5 Hz,1H), 4.37-4.43 (m, 4...

Embodiment 2

[0018] 33.4 mg (0.1 mmol) (tert-butoxycarbonyl)(3-(p-tolyl)isoquinolin-2-ium-2-yl)amide (R1=hydrogen, R2=p-methylphenyl, R3=tert-butyryl, R4=ethyl), 27.6 mg (0.2 mmol) Diethyl phosphite, 27.6 mg (0.2 mmol) K 2 CO 3 , 1.9 mg (0.01 mmol) CuI was added to the reaction test tube, then 2 mL of DCE was added, at 120 o The crude product was obtained by heating and reacting at C for 24 hours, cooled after the reaction, filtered, the filtrate was rotary evaporated, and the solvent was removed. The residue was subjected to silica gel column chromatography, washed with petroleum ether, and detected by TLC. The solvent was distilled off, and dried in vacuo to obtain 30.2 mg of diethyl (3-(p-tolyl)isoquinolin-1-yl)phosphonate as a pale yellow liquid, with a yield of 85%. 1 H NMR (500 MHz, CDCl 3 ) δ 8.91 (d, J = 8.4 Hz, 1H), 8.13(s, 1H), 8.06 (d, J = 8.0 Hz, 2H), 7.85 (d, J = 8.0 Hz, 1H), 7.64 (dt, J =15.1, 7.2 Hz, 2H), 7.30 (d, J = 7.5 Hz, 2H), 4.59 – 4.22 (m, 4H), 2.41 (s,3H...

Embodiment 3

[0020] 30.0 mg (0.1 mmol) (tert-butoxycarbonyl)(3-butylisoquinolin-2-ium-2-yl)amide (R1=hydrogen, R2=butyl, R3=tert-butyryl, R4=ethyl), 27.6 mg (0.2 mmol) diethyl phosphite, 27.6 mg (0.2 mmol) K 2 CO 3 , 1.9 mg (0.01 mmol) CuI was added to the reaction test tube, and then 2 mL of DCE was added, at 120 oThe crude product was obtained by heating and reacting at C for 24 hours, cooled after the reaction, filtered, the filtrate was rotary evaporated, and the solvent was removed. The residue was subjected to silica gel column chromatography, washed with petroleum ether, and detected by TLC. The solvent was distilled off, and dried in vacuo to obtain 28.0 mg of diethyl (3-butylisoquinolin-1-yl) phosphonate as a pale yellow liquid, with a yield of 80%. 1 H NMR (500 MHz, CDCl 3 ) δ 8.87 (d, J = 8.5 Hz, 1H), 7.77 (d, J = 8.0 Hz,1H), 7.65 (t, J = 7.5 Hz, 1H), 7.62 – 7.51 (m, 2H), 4.56 – 4.15 (m, 4H), 2.99(t, J = 7.6 Hz, 2H), 1.95 – 1.70 (m, 2H), 1.41 (m, 8H), 0.95 (t, J = 7...

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 preparation method of an isoquinoline phosphite ester compound. The method comprises the following steps: selecting an isoquinoline nitrogen compound as a substrate, adding phosphite ester into the substrate, then taking 1, 2 dichloroethane as a solvent, and performing thermal reaction in the air with the combined action of an alkaline condition and a copper catalyst, soas to obtain a crude product. Through the adoption of the method, the production is low, the compound yield is high, and the method is applicable to industrial promotion.

Description

technical field [0001] The invention relates to a preparation method of isoquinoline phosphite compounds. Background technique [0002] Quinoline is an important part of organic synthesis. Compounds containing isoquinoline structures are widely found in medicines, natural products and organisms. Isoquinoline phosphites are an important class of compounds that are widely used in organic synthesis. [0003] Related literature Bo Yao (Chem. Commun., 2015, 51, 4097) discloses a method for efficiently synthesizing isoquinoline phosphite compounds through palladium-catalyzed β-position activation of isoquinoline nitrogen oxide compounds, that is, using isoquinoline Phenyl nitrogen oxides are substrates, tertiary amines are added to substrates, and Pd(MeCN) 2 Cl 2 As a catalyst, with DMF and DMA as a mixed solvent, with Yb 2 o 3 As a base, tetrabutylammonium acetate is used as an additive, and the crude product is obtained through a heating reaction. [0004] Though said meth...

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): C07F9/62
CPCC07F9/62
Inventor 邓辰亮张兴国张小红詹鑫晨
Owner WENZHOU UNIVERSITY
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