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A kind of preparation method of o-iodoaniline

A technology for 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 product yield of o-iodoaniline, difficult separation of isomers and the like, and achieves mild conditions, low price, high yield effect

Active Publication Date: 2020-04-03
GUIZHOU UNIV
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  • 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

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  • A kind of preparation method of o-iodoaniline
  • A kind of preparation method of o-iodoaniline
  • A kind of 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 that 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 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.

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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

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Application Information

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Patent Type & Authority Patents(China)
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
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