Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing 4-acetyl-1-naphthoic acid

A technology of naphthoic acid and acetyl group, applied in the field of preparing 4-acetyl-1-naphthoic acid, can solve the problems of high cost, low yield, low product yield and the like

Pending Publication Date: 2021-09-07
东莞市东阳光动物保健药品有限公司
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In the prior art, patent documents AU2005319305 and ChemCatChem, 9 (16), 3121-3124 all disclose the preparation technology of afolana intermediate (formula II), wherein, the method disclosed in AU2005319305 has low product yield, Have used dangerous reagent methylzinc, the shortcoming that part aftertreatment needs anhydrous environment; ChemCatChem, 9 (16), the method disclosed in 3121-3124 exists the formic acid that uses noble metal catalyst palladium acetate and seven times equivalent, and cost is higher, and productive rate Low, unsuitable for scale-up production

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
  • Method for preparing 4-acetyl-1-naphthoic acid
  • Method for preparing 4-acetyl-1-naphthoic acid
  • Method for preparing 4-acetyl-1-naphthoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Preparation of Example 1 Compound (2)

[0081]

[0082] Compound (1), namely 1,4 naphthalene dicarboxylic acid (80 g, 370 mmol) and methanol (560 mL) were added to a 1000 mL round-bottomed flask, the temperature was lowered to below 0 °C, and SOCl was slowly added dropwise with stirring. 2 (92.4 g, 777 mmol), after the dropwise addition was completed, the temperature was raised to 75° C., and the reaction was refluxed for 12 h. After the reaction was completed, it was lowered to room temperature, and the reaction solution was concentrated under reduced pressure to obtain a solid crude product. The crude product was dissolved in 300 mL of toluene, and 150 mL of 10% K 2 CO 3 (mass fraction) washed twice, then washed with 150 mL of water, separated the organic phase, and concentrated under reduced pressure to obtain compound (2): 86.0 g, yield 96%, purity 98.1%; detection:

[0083] 1 H NMR (400MHz, CDCl 3 )δ9.49–8.48(m,2H),8.09(s,2H),7.77–7.58(m,2H),4.03(s,6H).

Embodiment 2

[0084] Preparation of Example 2 Compound (2)

[0085] Compound (1), namely 1,4 naphthalene dicarboxylic acid (50 g, 231 mmol) and methanol (350 mL) was added to a 1000 mL round-bottomed flask, and concentrated sulfuric acid (47.6 g, 485.7 mmol) was slowly added dropwise with stirring. After the dropwise addition was completed, The temperature was raised to 75°C, and the reaction was refluxed for 12h. After the reaction, it was lowered to room temperature, and the reaction solution was concentrated under reduced pressure to obtain a solid crude product. The crude product was dissolved in 400 mL of toluene, and 100 mL of 10% K 2 CO 3 (mass fraction) was washed twice, then washed with 150 mL of water, the organic phase was separated, and concentrated under reduced pressure to obtain compound (2): 53.0 g with a yield of 93.8% and a purity of 95%.

Embodiment 3

[0086] Preparation of Example 3 Compound (2)

[0087] Compound (1), namely 1,4 naphthalene dicarboxylic acid (10 g, 46.2 mmol) and methanol (70 mL) was added to a 250 mL round-bottomed flask, and concentrated hydrochloric acid (11.5 mL, 138.6 mmol) was slowly added dropwise with stirring. , the temperature was raised to 75°C, and the reaction was refluxed for 12h. After the reaction was completed, it was lowered to room temperature, and the reaction solution was concentrated under reduced pressure to obtain a solid crude product. The crude product was dissolved in 100 mL of ethyl acetate, and 50 mL of 10% K 2 CO 3 (mass fraction) washed twice, then washed with 50 mL of water, separated the organic phase, concentrated under reduced pressure to obtain compound (2): 18.3 g, yield 81.1%, purity 95.7%.

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 method for preparing 4-acetyl-1-naphthoic acid, and belongs to the technical field of pharmacy. According to the method provided by the invention, 1, 4-naphthalic acid which is low in price and easy to obtain is taken as a raw material, and 4-acetyl-1-naphthoic acid is prepared by adding Meldrum's acid, performing decarboxylation to formylate carboxyl, and finally performing hydrolysis. According to the method provided by the invention, a high-purity product can be obtained, an inflammable metal reagent methyl zinc is not used in the process, the reaction condition is mild, the operation is simple, and the method is suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, in particular to a method for preparing 4-acetyl-1-naphthoic acid. Background technique [0002] Afoxolaner, CAS: 1093861-60-9, chemical name: 4-{(5R)-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl) Fluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl base}naphthalene-1-carboxamide, the molecular formula is C 26 H 17 ClF 9 N 3 O 3 , the molecular weight is 625.87. Aflana is a pet drug, mainly used as an oral in vitro deworming drug for dogs in clinical practice. [0003] The chemical structural formula of Aforana is shown in formula (I): [0004] [0005] 4-Acetyl-1-naphthoic acid and its derivatives are the key intermediates in the synthesis of aflana, and the chemical structural formula of 4-acetyl-1-naphthoic acid is shown in formula (II): [0006] [0007] In the prior art, both the patent documents AU20...

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): C07C51/38C07C65/32C07D319/06
CPCC07C51/38C07D319/06C07C67/313C07C67/08C07C65/32C07C69/76
Inventor 王仲清李东明陈永好范炜隆张梦辉黄芳芳
Owner 东莞市东阳光动物保健药品有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com