Method for preparing 2-chloroquinoline-3-boric acid

A technology of chloroquine and boric acid, which is applied in the field of organic chemical synthesis, can solve the problems of waste of manpower and material resources, complex preparation methods, etc., and achieve the effects of simple operation, simple post-treatment purification, and high yield

Pending Publication Date: 2021-06-22
陕西维世诺新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the existing 2-chloroquinoline-3-boronic acid is prepared from the raw material 3-bromoquinoline, which is oxidized into 3-bromoquinoline nitrogen oxide through peroxide, and then rearranged, a

Method used

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  • Method for preparing 2-chloroquinoline-3-boric acid
  • Method for preparing 2-chloroquinoline-3-boric acid

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Under nitrogen, 400 ml of tetrahydrofuran and 2-chloroquinoline (40 g; 0.25 mol) were successively added into a 1000 ml three-necked flask. Start stirring, lower the temperature to -40°C, react for 0.5 hours, then add lithium diisopropylamide (150ml, 0.38mol) dropwise, keep the temperature at -40°C for one hour, then start to add triisopropyl borate (71g, 0.38mol) dropwise. mol), the reaction was incubated for two hours.

[0048] Post-treatment: Add 400ml of 1mol / L dilute hydrochloric acid to the reaction to quench the reaction, extract the system with 400ml of ethyl acetate, separate the organic phase, and dry the organic phase (drying with anhydrous magnesium sulfate at room temperature for 1 to 3 hours) Concentrate under reduced pressure (at a temperature of 30-50° C., use a vacuum water pump to bring it into a negative pressure state, and remove tetrahydrofuran and ethyl acetate in the system), and recrystallize with petroleum ether to obtain 39.1 g of a white solid...

Embodiment 2

[0050] Under nitrogen, 400 ml of ether and 2-chloroquinoline (40 g; 0.25 mol) were successively added into a 1000 ml three-neck flask. Start stirring, lower the temperature to -60°C, react for 0.5 hours, then add n-butyllithium (150ml, 0.38mol) dropwise, keep the temperature at -60°C for one hour, then start to add triisopropyl borate (71g, 0.38mol) dropwise , heat preservation reaction for two hours.

[0051] Post-treatment: Add 400ml of 1mol / L dilute hydrochloric acid to the reaction to quench the reaction, extract the system with 400ml of ethyl acetate, separate the organic phase, and dry the organic phase (drying with anhydrous magnesium sulfate at room temperature for 1 to 3 hours) Concentrate under reduced pressure (at a temperature of 30-50°C, use a vacuum water pump to bring it into a negative pressure state to remove tetrahydrofuran and ethyl acetate in the system), and recrystallize twice with petroleum ether to obtain 22.9 g of a white solid. HPLC=99%, the yield is...

Embodiment 3

[0053] Under nitrogen, 400ml of 2-methyltetrahydrofuran and 2-chloroquinoline (40g; 0.25mol) were successively added into a 1000ml three-neck flask. Start stirring, lower the temperature to -30°C, react for 0.5 hours, then add lithium diisopropylamide (150ml, 0.38mol) dropwise, keep the temperature at -30°C for one hour, then start to add triisopropyl borate (71g, 0.38mol) dropwise. mol), the reaction was incubated for two hours.

[0054] Post-treatment: Add 400ml of 1mol / L dilute hydrochloric acid to the reaction to quench the reaction, extract the system with 400ml of ethyl acetate, separate the organic phase, and dry the organic phase (drying with anhydrous magnesium sulfate at room temperature for 1 to 3 hours) Concentrate under reduced pressure (at a temperature of 30-50°C, use a vacuum water pump to bring it into a negative pressure state to remove tetrahydrofuran and ethyl acetate in the system), and recrystallize with petroleum ether to obtain 30.0 g of a white solid. ...

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for preparing 2-chloroquinoline-3-boric acid. The existing preparation method of 2-chloroquinoline-3-boric acid is relatively complex and wastes manpower and material resources. The invention provides the method for preparing 2-chloroquinoline-3-boric acid, which comprises the following steps: taking 2-chloroquinoline and a boron reagent as raw materials, carrying out 3-site substitution reaction on the 2-chloroquinoline under the action of alkali, and then hydrolyzing under the action of acid to obtain the 2-chloroquinoline-3-boric acid. The method has the advantages of mild reaction conditions, simple post-treatment purification, high yield and low cost.

Description

technical field [0001] The application belongs to the technical field of organic chemical synthesis, in particular to a method for preparing 2-chloroquinoline-3-boronic acid. Background technique [0002] The melting point of 2-chloroquinoline-3-boronic acid is 144-147°C, the boiling point is 426.2±55.0°C (Predicted), the density is 1.42±0.1g / cm3 (Predicted), the storage condition is 2-8°C, and the acidity coefficient (pKa ) Chemicalbook: 5.62±0.30 (Predicted), InChIKey is JAQXYUOPSOXQCG-UHFFFAOYSA-NCAS, database is 128676-84-6 (CASDataBaseReference). 2-Chloroquinoline-3-boronic acid (128676-84-6) is generally not hazardous to water. Calculate the chemical data as 1. The number of hydrogen bond donors, 22. The number of hydrogen bond acceptors, 33. The number of rotatable chemical bonds, 14. The topological molecular polar surface area (TPSA) is 53.45, the number of heavy atoms is 14, and the storage conditions are if It will not decompose when used and stored in accordanc...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 吕钟毕永林
Owner 陕西维世诺新材料有限公司
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