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Novel synthetic method of 7-hydroxy-3,4-dihydroquinolines

A technique for the synthesis of dihydroquinolones and methods, which is applied in the field of new synthesis of 7-hydroxy-3,4-dihydroquinolones, which can solve the problems of low reaction yield and large pollution, and achieve good selectivity and low discharge of three wastes , the effect of high yield

Active Publication Date: 2008-11-12
ZHEJIANG BENLI TECH CO LTD
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve the problems of low reaction yield and large pollution in the above-mentioned process, the present invention provides a synthetic method of 7-hydroxy-3,4-dihydroquinolone with reasonable process, simple and convenient operation, and less discharge of three wastes

Method used

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  • Novel synthetic method of 7-hydroxy-3,4-dihydroquinolines

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Embodiment 1

[0026] Embodiment 1: Synthesis of N-(3-chloropropionyl)-3-hydroxyaniline

[0027] Add 25.0g (0.229mol) of 3-hydroxyaniline, 19.3g (0.230mol) of sodium bicarbonate, 0.25g of tetrabutylammonium chloride and 200ml of water into a 500ml three-necked flask, stir and cool the reaction solution with ice water to 5 ~10°C, slowly add 29.3g (0.230mol) 3-chloropropionyl chloride dropwise, after the dropwise addition, keep it warm at 5~10°C for about 1.5 hours, filter under reduced pressure, wash the filter cake with water, and then evaporate to dryness 41.2 g of white solid, namely N-(3-chloropropionyl)-3-hydroxyaniline, was obtained with a yield of 90.2%, mp: 132°C, and a purity of 99.4% by HPLC.

Embodiment 2

[0028] Embodiment 2: Synthesis of 7-hydroxyl-3,4-dihydroquinolones

[0029] Put 15.0g (0.075mol) of N-(3-chloropropionyl)-3-hydroxyaniline and 15.0g of HZSM-5 molecular sieve into a reaction flask, heat up to melt the reactants, and keep stirring at about 160°C for about 1 hour , TLC tracking reaction is complete, after cooling slightly, add 300ml of water in the reaction bottle, reflux and stir for about 1 hour, filter while hot to reclaim molecular sieve, the filtrate is cooled and crystallized, and the crystal is recrystallized with 300ml of water to obtain 8.6g of white crystal product. That is, 7-hydroxy-3,4-dihydroquinolone, the yield is 70.3%, mp: 233°C-235°C, and the purity by HPLC is 99.0%.

Embodiment 3

[0030] Embodiment 3: Synthesis of N-(3-chloropropionyl)-3-hydroxyaniline

[0031] Add 32.7g (0.300mol) of 3-hydroxyaniline, 27g (0.321mol) of sodium bicarbonate, 0.33g of tetrabutylammonium chloride and 250ml of water into a 500ml three-necked flask, stir and cool the reaction solution with ice water to 5~ Slowly add 41.9g (0.330mol) of 3-chloropropionyl chloride dropwise at 10°C. After the dropwise addition, keep the reaction at 5-10°C for about 2 hours, filter under reduced pressure, wash the filter cake with water, and then dry it by rotary evaporation. 54.0 g of white solid, namely N-(3-chloropropionyl)-3-hydroxyaniline, was obtained with a yield of 90.2%.

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Abstract

The invention discloses a novel synthesis method for 7-Hydroxy-3,4-dihydroquinolone. The method is as follows: as shown in a formula (II), N-(3-chloropropionyl)-3-aminophenol undergoes intramolecular friedel-craft alkylation under the catalysis of solid acid catalyst at a temperature of between 132 and 200 DEG C, added with a solvent for elution after the reaction completes, filtered to reclaim the catalyst. The filtrate is cooled and crystallized to give the 7-Hydroxy-3,4-dihydroquinolone shown in a formula (I). The synthesis method for 7-Hydroxy-3,4-dihydroquinolone of the invention has the advantages of reasonable process, simple operation, high yield rate, low discharge of three waste gases, excellent application value.

Description

(1) Technical field [0001] The invention relates to a new synthetic method for synthesizing an important intermediate of the third-generation novel atypical antipsychotic drug aripiprazole—7-hydroxyl-3,4-dihydroquinolone. (2) Background technology [0002] According to literature reports, the synthesis of 7-hydroxyl-3,4-dihydroquinolone mainly contains the following two methods: one is to use 2-nitro 4-methoxyaniline as raw material to prepare 2-nitro-4-methoxyaniline earlier. Oxybenzaldehyde is obtained through five steps of condensation, esterification, hydrogenation and ring closure, and demethylation. This method has many reaction steps, and the total yield is lower than 20%. Another method is to use m-aminoanisole as a raw material, through the acylation of the amino group with 3-chloropropionyl chloride, and then through the intramolecular Friedel-Crafts alkylation reaction. The method yield is higher, but adopts a large amount of AlCl 3 As a catalyst, the environme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227
CPCY02P20/584
Inventor 顾海宁李小玲张习坤汪劲松
Owner ZHEJIANG BENLI TECH CO LTD
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