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Method for synthesizing 8-hydroxyjulolidine

A synthesis method, 3-Y technology, applied in directions such as organic chemistry, can solve problems such as low yield, unfavorable industrial production, etc., and achieve the effect of high reaction yield

Inactive Publication Date: 2019-08-20
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The yield of this method is low, and the product also needs to be purified by column chromatography, which is not conducive to industrial production

Method used

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  • Method for synthesizing 8-hydroxyjulolidine
  • Method for synthesizing 8-hydroxyjulolidine
  • Method for synthesizing 8-hydroxyjulolidine

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Experimental program
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Embodiment approach

[0025] The synthesis method of 8-hydroxyjuloridine in one embodiment comprises the following steps S110-S130:

[0026] S110, 3-methoxyaniline, X-(CH 2 ) 3 -Y reacts with the inorganic base under heating conditions, divides water during the reaction, cools after the reaction, adds water to separate the layers, takes the organic layer and extracts it with a strong acid, and combines the water layer. After the combined water layer is neutralized with alkali, it is extracted, Concentrate under reduced pressure to obtain crude 8-methoxyjuloridine.

[0027] Wherein, X and Y are independently selected from Br or Cl. That is, X-(CH 2 ) 3 -Y is 1,3-dibromopropane Br-(CH 2 ) 3 -Br, 1,3-dichloropropaneCl-(CH 2 ) 3 -Cl or 1-bromo-3-chloropropane Br-(CH 2 ) 3 -Cl.

[0028] Further, 3-methoxyaniline and X-(CH 2 ) 3 The molar ratio of -Y is 1:(6.5~15).

[0029] Further, the inorganic base is at least one selected from sodium carbonate, potassium carbonate, sodium bicarbonate, p...

Embodiment 1

[0058] 1-bromo-3-chloropropane (62.6kg, 398mol) and 3-methoxyaniline (6.53kg, 53.0mol) were pumped into the 100L reactor, then anhydrous sodium carbonate (17.0kg, 160mol) was added under stirring ). After the addition, stir at 65°C for 3 hours, then raise the temperature to 100°C to continue the reaction until the complete conversion of 3-methoxyaniline, during which the generated water will leave the reaction system. After the reaction, cool to 60°C, add water layer, and extract the organic layer with 15% hydrochloric acid. The combined aqueous layers were adjusted to pH 8-9 with 30% sodium hydroxide solution, and then extracted with ethyl acetate. The solvent was distilled off under reduced pressure to obtain the crude product of 8-methoxyjuloridine (11.0kg).

[0059] 40% hydrobromic acid (36.4 kg) was added to the crude 8-methoxyjuloridine obtained in the previous step (11.0 kg), and the resulting mixture was stirred at 100° C. for 20 hours. After the reaction, cool to 5...

Embodiment 2

[0068] Pump 1,3-dichloropropane (89.8kg, 795mol) and 3-methoxyaniline (6.53kg, 53.0mol) into a 100L reactor, and then add sodium bicarbonate (13.4kg, 160mol) under stirring. After the addition, stir at 95°C for 2 hours, then raise the temperature to 150°C to continue the reaction until the complete conversion of 3-methoxyaniline, during which the generated water will go out of the reaction system. After the reaction, cool to 70°C, add water layer, and extract the organic layer with 15% hydrochloric acid. The combined aqueous layers were adjusted to pH 8-9 with 30% sodium hydroxide solution, and then extracted with ethyl acetate, and the solvent was distilled off under reduced pressure to obtain crude 8-methoxyjuloridine (10.9 kg).

[0069] 40% hydriodic acid (57.6 kg) was added to the crude 8-methoxyjuloridine obtained in the previous step (10.9 kg), and the resulting mixture was stirred at 110° C. for 16 hours. After the reaction, cool to 60°C and filter to obtain the crude ...

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Abstract

The invention relates to a method for synthesizing 8-hydroxyjulolidine. The method comprises the following steps: reacting 3-methoxyaniline, X-(CH2)3-Y and an inorganic base under a heating condition,separating water during the reaction, and carrying out post-treatment after the completion of the reaction to obtain crude 8-hydroxyjulolidine; mixing the crude 8-hydroxyjulolidine with a halogen acid, heating the obtained mixture to react the mixture, and cooling and filtering the obtained solution after the reaction is completed in order to obtain a halogen acid salt of 8-hydroxyjulolidine; andmixing the halogen acid salt of 8-hydroxyjulolidine with water, neutralizing the obtained solution with a base, and carrying out extraction, drying, reduced pressure concentrating, beating and purification to obtain the 8-hydroxyjulolidine. The method has the advantages of abandoning of traditional column chromatography purification, suitableness for industrial production, and high yield.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of 8-hydroxyjuloridine. Background technique [0002] Coumarin exhibits good characteristics of tunable wavelength, high quantum yield, high absorption coefficient, and small overlap in absorption and emission spectra, so it is usually used as laser fuel and fluorescent probe for biological assays. 8-Hydroxyjuloridine is an important precursor substance for the synthesis of coumarin, and its structural formula is as follows: [0003] [0004] CN107880052A discloses a kind of synthetic method of 8-hydroxyjuloridine, in nitrogen atmosphere, 3-methoxyaniline (1.3g, 10.0mmol), 1-bromo-3-chloropropane (20.0g, 128.0mmol ) was stirred at room temperature for 0.5 hours, then the reaction system was heated to 95° C. for 1 hour, then the temperature was raised to 140° C. to continue the reaction for 24 hours, and finally the entire reaction system was heat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/04
CPCC07D455/04
Inventor 傅长金邓泽平吴四清陈毅征许慧
Owner 湖南华腾制药有限公司
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