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

2-methyl-3-hydroxy-6-isopropylquinoline-4-carboxyl acid preparation method

A technology of isopropylquinoline and isopropylaniline, applied in the field of synthesis of organic intermediates, can solve problems such as being difficult to obtain, unsuitable for industrialization, and high corrosiveness of equipment, and achieves improved reaction speed, easy industrialization, and safe operation. Effect

Inactive Publication Date: 2006-05-03
CHINA LUCKY FILM CORP +1
View PDF1 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are following disadvantages in the disclosed above-mentioned preparation method: (1) use hydroxyacetone to prepare 4-carboxylic acid, although the yield is very high, but hydroxyacetone is unstable, the raw material is not easy to get and the cost is high; (2) adopt indigo to prepare indigo Red, and then prepare 4-carboxylic acid, the yield is higher, but indigo is as a kind of dye intermediate, and the cost of itself is higher, and source is limited, is difficult for obtaining; (3) adopt p-methylaniline as raw material synthesis 5- Methyl isatin requires the use of nitrobenzene as a solvent, which is highly toxic and has the risk of explosion. In addition, hydrogen chloride gas is required in the reaction. Hydrogen chloride gas is extremely corrosive to equipment and is not suitable for industrialization.

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
  • 2-methyl-3-hydroxy-6-isopropylquinoline-4-carboxyl acid preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 16.5 grams of chloral hydrate and 142 grams of sodium sulfate aqueous solution in a 500 milliliter reaction flask, then add 13.5 grams of p-cymeniline, 10 milliliters of concentrated hydrochloric acid and 20.8 grams of hydroxylamine hydrochloride, heat the mixture to 60 ° C, After reacting for 3 hours, it was cooled to room temperature and filtered to obtain 4-isopropyloximinoacetoethylamine as a yellow-brown solid.

[0021] In a 250 ml reaction flask, add solid 4-isopropyloximinoacetoethylamine and 35 grams of concentrated sulfuric acid, stir to dissolve, heat to 80°C, react for 0.5 hours and cool to room temperature, add the reaction solution to ice water to precipitate, Filtration yielded 9.4 g of a reddish-brown 5-isopropyl-isatin solid.

[0022] In a 500ml reaction flask, add 10g of calcium oxide and 350ml of water, stir to dissolve, then add the ethanol solution of isatin obtained in the previous step, heat to 80°C, then add 9.3g of chloroacetone dropwise, and...

Embodiment 2

[0024] In a 500 ml reaction flask, add 33 g of chloral hydrate and 142 g of potassium sulfate in water, then add 13.5 g of p-cymeniline, 10 ml of concentrated hydrochloric acid and 34.7 g of hydroxylamine hydrochloride, and heat the mixture to 100°C. After reacting for 2 hours, it was cooled to room temperature and filtered to obtain 4-isopropyloximinoacetoethylamine as a yellow-brown solid.

[0025] In a 250 ml reaction flask, add solid 4-isopropyloximinoacetoethylamine and 70 g of concentrated sulfuric acid, stir to dissolve, stir and react at 60°C for 1 hour, cool down to room temperature, add the reaction solution to ice water to precipitate, Filtration yielded 9.4 g of a reddish-brown 5-isopropyl-isatin solid.

[0026] In a 500ml reaction flask, add 10g of calcium oxide and 350ml of water, stir to dissolve, add the ethanol solution of isatin obtained in the previous step, heat to 80°C, add 9.3g of chloroacetone dropwise, and continue the reaction at 100°C for 5 Hour. Th...

Embodiment 3

[0028] Add 49.5 grams of chloral hydrate and an aqueous solution of 142 grams of sodium sulfate in a 500 milliliter reaction flask, then add 13.5 grams of p-cymeniline, 10 milliliters of concentrated hydrochloric acid and 20.8 grams of hydroxylamine hydrochloride. The mixture was heated to 40° C., cooled to room temperature after 4 hours of reaction, and filtered to obtain 4-isopropyloximinoacetoethylamine as a yellow-brown solid. .

[0029] In a 250ml reaction bottle, add solid 4-isopropyloximinoacetoethylamine and 50 grams of concentrated sulfuric acid, stir to dissolve, heat to 70°C and stir for 0.5 hours, cool down to room temperature, add the reaction solution to ice water to precipitate , filtered to obtain 9.2 g of reddish-brown 5-isopropyl-isatin solid

[0030] In a 500 ml reaction bottle, add 10 grams of calcium hydroxide and 350 ml of water, stir to dissolve, add the ethanol solution of isatin obtained in the previous step, heat to 60 ° C, then add 13.9 grams of chl...

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 preparation method for 2- methyl -3-hydroxyl -6- isopropylquinoline-4- hydroxy acid, which comprises: adding chloral and inorganic salt liquid into reaction bulb, as well as p-isopropoxyphenylamine and strong hydrochloric acid and hydroxylamine hydrochloride, obtaining 4-isopropyloximinoacetamide solid; adding strong sulphuric acid, heating, stirring, cooling; pouring reaction liquid into ice water, filtering to obtain 5- isopropyl-isatin solid; with calcium oxide or calcium hydroxide, adding 5- isopropyl-isatin solid into reaction bulb, heating, dropping chloracetone; then neutralizing with acid to obtain golden-ocher product. This invention is simple and security.

Description

technical field [0001] The invention relates to a method for synthesizing an organic intermediate used in dye synthesis, in particular to a method for synthesizing 2-methyl-3-hydroxyl-6-isopropylquinoline-4-carboxylic acid. Background technique [0002] 2-Methyl-3-hydroxyl-6-isopropylquinoline-4-carboxylic acid (3-hydroxy-2-methyl-6-isopropylquinoline-4-carboxylic acid) is referred to as isopropylquinoline-4-carboxylic acid, is A relatively new compound. So far, the reports about this compound are only limited to its application, but there is no literature report about the synthesis of this compound. [0003] There are data reports on the preparation method of 4-carboxylic acid compounds similar to isopropyl-4-carboxylic acid structure, such as the introduction of the use of isatin and hydroxyacetone in the German patent DE2249067 to prepare 4-carboxylic acid compound 2-methanone Base-3-hydroxyquinoline-4-carboxylic acid, the yield reaches 98.6%; for the preparation of isa...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/50
Inventor 赵宗琳
Owner CHINA LUCKY FILM CORP
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