Check patentability & draft patents in minutes with Patsnap Eureka AI!

Preparation method of 2-hydroxy-3-nitroacetophenone

A technology of nitroacetophenone and hydroxyl, applied in the field of medicine, can solve the problems of little industrial significance, poor yield selectivity, and expensive raw materials

Pending Publication Date: 2022-05-10
南京焕然生物科技有限公司
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield selectivity of this method is poor, and after preparative chromatographic separation, the productive rate is 30%; the raw materials used are more expensive, and the industrialization significance is not great

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 2-hydroxy-3-nitroacetophenone
  • Preparation method of 2-hydroxy-3-nitroacetophenone
  • Preparation method of 2-hydroxy-3-nitroacetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A preparation method of 2-hydroxyl-3-nitroacetophenone, specifically comprising the following steps:

[0030] (1) Add 700ml of dichloromethane into the reaction flask, add 94.1g of phenol and 161.6g of N-methylmorpholine under stirring, slowly add 123.8g of chlorothiomethane dropwise at a temperature of 20°C~30°C, and stir after adding React for 10 hours, concentrate to dryness under reduced pressure, add 800ml of ethyl acetate and 300ml of water, stir and separate the liquids, dry the organic phase with anhydrous sodium sulfate, decolorize with activated carbon under reflux, filter, concentrate the filtrate to dryness, and wash with 250ml of toluene Recrystallized, filtered and dried to obtain 120.1 g of intermediate Ⅰ, a reddish solid, with a yield of 85.7%.

[0031] (2) Add 1100ml of ethanol to the reaction flask, add 120.1g of intermediate I under stirring, add 266.1g of ferric nitrate in batches under temperature control at 50°C~60°C, and react for 14 hours after a...

Embodiment 2

[0035] A preparation method of 2-hydroxyl-3-nitroacetophenone, specifically comprising the following steps:

[0036] (1) Add 900ml of tetrahydrofuran into the reaction flask, add 94.1g of phenol and 90.6g of copper diacetate under stirring, slowly add 103.6g of dimethyl disulfide dropwise under the condition of keeping warm at 50°C~60°C, and stir for 24 hours after completion of the reaction , concentrated to dryness under reduced pressure, added 800ml of ethyl acetate and 300ml of water, stirred and left to separate the liquids, the organic phase was dried with anhydrous sodium sulfate and then decolorized with activated carbon under reflux, filtered, the filtrate was concentrated to dryness, recrystallized with 250ml of toluene, Filtration and drying yielded 110.1 g of intermediate I as a reddish solid with a yield of 78.5%.

[0037] (2) Add 800ml of acetic acid into the reaction flask, add 110.1g of intermediate I under stirring, add 86.1g of nitric acid with a mass concent...

Embodiment 3

[0041] (1) Add 1100ml of chloroform into the reaction flask, add 94.1g of phenol and 146.8g of anhydrous aluminum trichloride under stirring, slowly add 141.3g of dimethyl disulfide dropwise under the condition of keeping warm at 40°C~50°C, add After stirring and reacting for 6 hours, concentrate under reduced pressure to dryness, add 800ml of ethyl acetate and 300ml of water, stand for liquid separation after stirring, stand for liquid separation after stirring, dry the organic phase with anhydrous sodium sulfate, decolorize with activated carbon under reflux, and filter , the filtrate was concentrated to dryness, recrystallized with 250 ml of toluene, filtered and dried to obtain 103.9 g of intermediate I, an off-white solid, with a yield of 74.1%.

[0042](2) Add 600ml of acetonitrile into the reaction flask, add 103.9g of intermediate I under stirring, add 133.9g of tert-butyl nitrite dropwise under temperature control at 30°C~40°C, react for 48 hours after addition, and co...

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

No PUM Login to View More

Abstract

The invention relates to a preparation method of 2-hydroxy-3-nitroacetophenone, in particular to a method for efficiently synthesizing 2-hydroxy-3-nitroacetophenone by taking phenol as a raw material through four steps of methyl vulcanization, nitration, acetylation and desulfurization. The preparation method of the 2-hydroxy-3-nitroacetophenone provided by the invention is a preparation method which is high in yield, low in cost, less in three wastes, good in product quality and suitable for industrialization.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a preparation method of 2-hydroxy-3-nitroacetophenone. Background technique [0002] 2-Hydroxy-3-nitroacetophenone is the starting material of leukotriene receptor antagonist-Pranlukast, and its main synthetic route is as follows: [0003] method 1: [0004] [0005] "Journal of Medicinal Chemistry" (Journal of Medicinal Chemistry, Mark Cushman, 1994, vol. 37, # 20, p. 3353 - 3362) discloses a method in which o-hydroxyacetophenone is used as a raw material to obtain the target product through nitration. The selectivity of this method is extremely poor, the yield is only 33%, and the p-nitrosylated product is generated in nearly equal amounts; the separation of the two nitro isomers is difficult and does not meet the requirements of environmental protection. [0006] Method 2: [0007] [0008] In the method disclosed in US4977162, the method uses 1-phenyl-2-hydroxyeth...

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): C07C201/12C07C205/45C07C319/14C07C319/20C07C323/20C07C323/22
CPCC07C201/12C07C319/14C07C319/20C07C323/20C07C323/22C07C205/45
Inventor 王坤鹏韩月林
Owner 南京焕然生物科技有限公司
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com