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

Preparation method of o-iodoaniline

A technology of o-iodoaniline and p-iodoaniline, which is applied in the field of o-iodoaniline and its preparation, can solve the problems of poor selectivity, low yield of o-iodoaniline products, difficult separation of isomers, etc., and achieves mild conditions, low price, The effect of high yield

Active Publication Date: 2017-03-29
GUIZHOU UNIV
View PDF2 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Direct iodination synthesis of o-iodoaniline products has disadvantages such as low yield, poor selectivity, and difficult separation of isomers.

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 o-iodoaniline
  • Preparation method of o-iodoaniline
  • Preparation method of o-iodoaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Preparation of p-iodoaniline

[0019] Add 4.1g of sodium bicarbonate, 3.1g of aniline and 50.0mL of ultrapure water into a conical flask equipped with magnetic stirring. After completely dissolving, the solution is cooled to 12.0-15.0°C under the action of a low-temperature thermostat, and stirred vigorously for 30 minutes. Add 0.024 mol (6.1 g) of iodine in batches, react for 80 min, and filter under reduced pressure to obtain a dark gray solid crude product. Wash with sodium bisulfite, ultrapure water and dry. Add 4.5 g of the dried crude product to a round bottom flask, add cyclohexane, and heat the solution to boil. After heating for about 5 minutes, wait for it to cool slightly, add activated carbon to decolorize, and quickly filter the hot solution in a hot state to remove insoluble impurities. The resulting solution crystallized on cooling. The crystals were obtained by suction filtration, washed with cyclohexane and ultrapure water, and dried to obtain th...

Embodiment 2

[0023] Add 10.0 g of p-iodoaniline (the synthesis method is the same as in Example (1)), 40.0 g of aniline, and 1.0 g of o-iodoaniline into a three-necked flask, and heat and react at 186.0-192.0° C. for 60 min. The resulting mixture solution was distilled off to remove most of the aniline and the residue was collected. The residue was heated with 100.0 g of n-hexane at 85.0-95.0°C for 30 min, and after cooling slightly, the upper layer of n-hexane solution was separated and frozen for crystallization. The crystals were washed with n-hexane and ultrapure water, and dried in air. Then use a mixed solvent of dichloromethane and ethyl acetate as the eluent, separate by column chromatography, evaporate the solvent under reduced pressure, and crystallize to obtain o-iodoaniline c in the form of white needles. Yield: 2.3g, 23%, white needle-like crystals; melting point (M.p.) 56.3-58.2°C.

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

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a preparation method of o-iodoaniline. The synthesis route is represented by a formula in the invention. The preparation method possesses following advantages: raw material aniline is widely available and cheap, and is beneficial for industrialized utilization of the preparation method; in a certain solvent, sodium bicarbonate / I2 are used for preparing paraiodoaniline via direct iodination of aniline, and yield is high; paraiodoaniline is taken as a raw material, a certain catalyst is adopted, and rearrangement reaction is carried out so as to realize chemical conversion of paraiodoaniline into o-iodoaniline, processing steps are few, conditions are mild, and green environment-protection requirements are satisfied; and both paraiodoaniline and o-iodoaniline are preferable pharmaceutical intermediates.

Description

technical field [0001] The invention relates to o-iodoaniline with cheap and easy-to-obtain starting materials and a simple process and a preparation method thereof. Background technique [0002] O-iodoaniline is an indispensable raw material for the preparation of medicines. O-iodoaniline is an important intermediate in the synthesis of indole and its derivatives, biological tryptophan drugs, quinoline derivatives, benzimidazole derivatives, itatoic anhydride, etc. At present, there are still many difficulties in synthesizing this type of o-iodoaniline compounds, especially products with higher purity, mainly including: (1) using p-iodoaniline in a solvent to convert o-iodoaniline into o-iodoaniline with hydriodic acid catalytic rearrangement , the yield of the product is not high, and the product is difficult to separate; (2) use p-iodoaniline in the aniline solvent, and convert it into o-iodoaniline by catalytic rearrangement with o-iodoaniline, and coking occurs easily ...

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): C07C17/12C07C17/35C07C25/02
CPCC07C17/12C07C17/35C07C25/02
Inventor 朱静李天祥张耀周亚利张明均
Owner GUIZHOU 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