A kind of preparation method of 2-hydroxyphenylpropiophenone

A technology of hydroxyphenylbenzene and hydroxybenzaldehyde, applied in the field of medical research, can solve problems such as difficult separation, difficult operation, and low yield, and achieve the effects of simple treatment, shortened reaction time, and short steps

Active Publication Date: 2021-09-21
CHANGZHOU RUIMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this process, para-isomers are produced during the rearrangement reaction, and the separation is difficult and the yield is low
Expensive catalysts are required for hydrogenation, and the requirements for technical equipment are relatively high, making it difficult to operate

Method used

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  • A kind of preparation method of 2-hydroxyphenylpropiophenone
  • A kind of preparation method of 2-hydroxyphenylpropiophenone
  • A kind of preparation method of 2-hydroxyphenylpropiophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] in N 2 Under protection, in a 3000ml four-neck flask, add 1500ml dichloroethane, 124g styrene and 122g salicylaldehyde, then add 5mol% PdCl 2 And 5mol% potassium phosphate, heated to 75 ° C for 6.5 hours. Cool down to room temperature, filter with suction, and wash the catalyst with a small amount of dichloroethane. The filtrate was evaporated to dryness to obtain a light yellow viscous liquid. Distilled under reduced pressure to obtain 194 g of a colorless transparent liquid with a yield of 85.8%.

Embodiment 2

[0031] in N 2 Under protection, in a 3000ml four-neck flask, add 1500ml dichloroethane, 124g styrene and 122g salicylaldehyde, then add 2.5mol% PdCl 2 And 2.5mol% potassium phosphate, heated to 75 ° C for 6.5 hours. Cool down to room temperature, filter with suction, and wash the catalyst with a small amount of dichloroethane. The filtrate was evaporated to dryness to obtain a light yellow viscous liquid. Distilled under reduced pressure to obtain 186 g of a colorless transparent liquid with a yield of 82.3%.

Embodiment 3

[0033] in N 2 Under protection, in a 3000ml four-neck flask, add 1500ml dichloroethane, 124g styrene and 122g salicylaldehyde, then add 5mol% PdCl 2 (the seventh recovery) and 5mol% potassium phosphate, the temperature was raised to 75° C. for 6.5 hours. Cool down to room temperature, filter with suction, and wash the catalyst with a small amount of dichloroethane. The filtrate was evaporated to dryness to obtain a light yellow viscous liquid. Distilled under reduced pressure to obtain 189 g of a colorless transparent liquid with a yield of 83.6%.

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Abstract

The present invention relates to a kind of preparation method of 2-hydroxyphenyl propiophenone, concrete steps are: in N 2 Under protection, styrene and 2-hydroxybenzaldehyde are used as raw materials, an organic solvent is added, a coupling reaction occurs in the presence of a noble metal catalyst, and an inorganic salt is added as an auxiliary catalyst to obtain 2-hydroxyphenylpropiophenone. The reaction of the invention is a one-step reaction with short steps and simple post-reaction treatment; the common palladium chloride is used to replace the expensive and rare catalyst, making industrialization possible; and the reaction time is greatly shortened by adding an auxiliary catalyst.

Description

technical field [0001] The invention relates to the field of medical research, in particular to a preparation method of 2-hydroxyphenylpropiophenone. Background technique [0002] Propafenone hydrochloride (propafenone hydrochloride), the chemical name is 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone hydrochloride, is a German The antiarrhythmic drug developed by Helopharm is a sodium channel blocker class Ic, which was first launched in Germany in 1979 and is mainly used clinically for the prevention and treatment of ventricular or supraventricular ectopic beats, ventricular or supraventricular tachycardia It can also be used to treat ischemic and refractory arrhythmias. [0003] 2-Hydroxyphenylpropiophenone is an important intermediate in the synthesis of propafenone hydrochloride. According to literature reports, the preparation process has the following two kinds. [0004] Method 1: Condensation of diethyl malonate and benzyl chloride, diethyl 2-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/69C07C49/83
CPCC07C45/69C07C49/83
Inventor 史卫明周禾王小亮
Owner CHANGZHOU RUIMING PHARMA
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