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Synthesis method of N-phenyl aminobenzoic acid

The technology of a phenylaminobenzene and a synthesis method is applied in the directions of chemical instruments and methods, preparation of carboxylic acid nitrile, preparation of organic compounds, etc., can solve the problems of toxicity and harm, high cost, low yield and the like, and achieves improved yield, Low cost and high yield

Pending Publication Date: 2020-12-29
SHANGHAI WOKAI BIOTECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the defects of low yield, high cost, and toxicity in the prior art N-phenylaminobenzoic acid synthesis method, the present invention provides a harmless, low-cost N-phenylaminobenzoic acid The synthetic method of the method adopts a one-pot process. Under the condition of not using a catalyst, reflux reaction is carried out with 2-chlorobenzonitrile and aniline in a solvent, and then the reflux reaction is continued in the water phase, and after being neutralized by dilute hydrochloric acid, Obtain the target product N-phenylaminobenzoic acid

Method used

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  • Synthesis method of N-phenyl aminobenzoic acid

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Embodiment 1

[0028] A kind of synthetic method of N-phenylaminobenzoic acid, comprises the steps:

[0029] (1) Dissolve 1.0mol 2-chlorobenzonitrile and 1.05mol aniline in 500mL of dried solvent DMSO, then add activated 0.1mol K 2 CO 3 And activated 3.0mol NaOH, heating to carry out a reflux reaction, the reaction time is 2h;

[0030] The activation is anhydrous K 2 CO 3 And solid NaOH is microwaved for 10-15min before use to remove surface moisture and gas, release its effective surface area, and increase its reactivity.

[0031] (2) After the reflux reaction is completed, recover 450mL of the solvent DMSO under reduced pressure, then cool the remaining liquid to 25°C, add 600mL of water, heat to boiling, and perform a second reflux reaction for 1.5h;

[0032] (3) Cool the reaction solution after the secondary reflux reaction in step (2) to room temperature, add dichloromethane to extract excess aniline, add dilute hydrochloric acid to neutralize to a pH value of 3-4 under stirring in ...

Embodiment 2

[0034] A kind of synthetic method of N-phenylaminobenzoic acid, comprises the steps:

[0035] (1) Dissolve 1.0mol 2-chlorobenzonitrile and 1.08mol aniline in 500mL of dried solvent DMSO, then add activated 0.3mol K 2 CO 3 And activated 3.2mol NaOH, heating to carry out a reflux reaction, the reaction time is 3h;

[0036] The activation is anhydrous K 2 CO 3 And solid NaOH is microwaved for 10-15min before use to remove surface moisture and gas, release its effective surface area, and increase its reactivity.

[0037] (2) After the reflux reaction is completed, recover 460mL of the solvent DMSO under reduced pressure, then cool the remaining liquid to 25°C, add 600mL of water, heat to boiling, and perform a second reflux reaction for 1.5h;

[0038] (3) Cool the reaction solution after the secondary reflux reaction in step (2) to room temperature, add dichloromethane to extract excess aniline, add dilute hydrochloric acid to neutralize to a pH value of 3-4 under stirring in ...

Embodiment 3

[0040] A kind of synthetic method of N-phenylaminobenzoic acid, comprises the steps:

[0041] (1) Dissolve 1.0mol 2-chlorobenzonitrile and 1.2mol aniline in 500mL of dried solvent DMSO, then add activated 0.5mol K 2 CO 3 And activated 3.5mol NaOH, heating to carry out a reflux reaction, the reaction time is 3h;

[0042] The activation is anhydrous K 2 CO 3 And solid NaOH is microwaved for 10-15min before use to remove surface moisture and gas, release its effective surface area, and increase its reactivity.

[0043] (2) After the reflux reaction is completed, recover 450mL of the solvent DMSO under reduced pressure, then cool the remaining liquid to 25°C, add 600mL of water, heat to boiling, and perform a second reflux reaction for 1.5h;

[0044] (3) Cool the reaction solution after the secondary reflux reaction in step (2) to room temperature, add dichloromethane to extract excess aniline, add dilute hydrochloric acid to neutralize to a pH value of 3-4 under stirring in t...

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Abstract

The invention belongs to the technical field of organic intermediate synthesis, and particularly relates to a synthesis method of N-phenyl aminobenzoic acid. The method comprises the following steps:(1) dissolving 2-chlorobenzonitrile and aniline in a solvent, adding K2CO3 and NaOH while stirring, and heating to carry out primary reflux reaction; (2) after the reflux reaction is finished, recovering the solvent under reduced pressure, then cooling the residual liquid, adding water, and heating to carry out secondary reflux reaction; and (3) cooling the reaction solution after the secondary reflux reaction in the step (2) to room temperature, extracting excessive aniline, adding diluted hydrochloric acid for neutralization while stirring a water phase, separating out a solid, filtering, and recrystallizing to obtain the target product N-phenyl aminobenzoic acid. According to the method, a one-pot process is adopted, under the condition that a catalyst is not used, 2-chlorobenzonitrileand aniline are used as raw materials for reaction, the target product with high purity (larger than 99%) and high yield (larger than 90%) is obtained, operation is easy, the raw materials are easy toobtain, the reaction is mild and easy to control, and aftertreatment is simple.

Description

technical field [0001] The invention belongs to the technical field of organic intermediate synthesis, and in particular relates to a synthesis method of N-phenylaminobenzoic acid. Background technique [0002] N-phenylaminobenzoic acid, also known as vanadium reagent, is an important intermediate commonly used in the synthesis of acridine compounds. At present, the common synthesis method of N-phenylaminobenzoic acid in the prior art is mainly to react anthranilic acid with halogenated benzene, and generate N-phenylaminobenzoic acid under the conditions of lead powder and nitrobenzene benzoic acid. But this method also has some disadvantages, such as nitrobenzene and lead powder are poisonous and harmful substances, which will cause great pressure to the human body and the environment, and the reaction yield is low. Also have some to adopt Ullman condensation method, take o-halobenzoic acid and aniline as main raw material, adopt copper-containing catalyst catalytic react...

Claims

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Application Information

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IPC IPC(8): C07C227/02C07C229/58
CPCC07C227/02C07C253/30C07C229/58C07C255/58
Inventor 陆惠懿郭建国柯德宏孙鑫李德峰
Owner SHANGHAI WOKAI BIOTECH