Synthesis method of aromatic amine carboxylic acid derivative

A technique for the synthesis of aromatic amine carboxylic acid and its synthesis method, which is applied in the field of synthesis of aromatic amine carboxylic acid derivatives, can solve problems such as insufficient variety, and achieve the effects of reasonable route design, high yield, and excellent pest control effect

Pending Publication Date: 2022-01-28
BEIJING YINONG BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthetic methods and types of the existing amide derivatives have been disclosed in previous patents, the types disclosed are not comprehensive enough, and there are many deficiencies in the preparation methods, yields, routes, etc.

Method used

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  • Synthesis method of aromatic amine carboxylic acid derivative
  • Synthesis method of aromatic amine carboxylic acid derivative
  • Synthesis method of aromatic amine carboxylic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] This example uses X 1 =F,R 2 =Phenyl is taken as an example for description, but the present invention is not limited to this embodiment.

[0033] Synthesis of ethyl 5-benzamido-2-fluoro-benzoate:

[0034]

[0035] Dissolve 5-amino-2-fluoro-benzoic acid ethyl ester (400 mg, 2.184 mmol, 1 equiv) in dichloromethane, and add benzoyl chloride (306.95 mg, 2.184 mmol, 1 equiv) successively at 0°C , pyridine (345.5 mg, 4.368 mmol, 2 equiv), after the addition was completed, the reaction was stirred at room temperature for 12 h, and TLC (PE / EA=3:1, Rf=0.5) was detected. After the reaction was completed, 20ml of 1N hydrochloric acid aqueous solution was added to wash the organic phase , extracted with ethyl acetate, combined the organic phases, and washed with water again, the organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off under negative pressure, and the crude product was purified by silica gel column (PE / EA=3:1) to obtain 5-benzyl Am...

Embodiment 2

[0039] This example uses X 1 =F,R 2 = phenyl, R 1 =Me as an example for description, but the present invention is not limited to this embodiment.

[0040] Synthesis of ethyl 2-fluoro-5-(N-methylbenzamido)benzoate:

[0041]

[0042] Dissolve ethyl 5-benzamido-2-fluoro-benzoate (1 g, 3.481 mmol, 1 equiv) in tetrahydrofuran (10 ml), under the protection of nitrogen, cool the liquid nitrogen to -78 °C, and start adding LiHMDS dropwise (0.87 g, 5.221 mmol, 1.5 equiv). After the dropwise addition, methyl iodide (0.74 g, 5.221 mmol, 1.5 equiv) was added dropwise for 10 min. After the addition was completed, the reaction was stirred at room temperature for 1 h, TLC (PE / EA =4:1, Rf=0.5) After the completion of the detection reaction, add 2ml of acetic acid at 0°C to quench the reaction, extract with ethyl acetate, combine the organic phases, wash with water again, dry the organic phases over anhydrous sodium sulfate, and steam under negative pressure The solvent was removed, and...

Embodiment 3

[0046] This example uses X 1 =F,R 2 = phenyl, R 1 =Me as an example for description, but the present invention is not limited to this embodiment.

[0047] Synthesis of 2-fluoro-5-(N-methylbenzamido)benzoic acid

[0048]

[0049] Ethyl 2-fluoro-5-(N-methylbenzamido)benzoate (750 mg, 2.489 mmol, 1 equiv), sodium hydroxide (199.11 mg, 4.978 mmol, 2 equiv) was added to water (10ml ), at 60°C, stirred for 2 hours, TLC (PE / EA=1:1, Rf=0.4) detected the reaction, cooled down to room temperature, added 1N hydrochloric acid aqueous solution to adjust to PH=2, extracted with ethyl acetate, The organic phase was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under negative pressure to obtain 2-fluoro-5-(N-methylbenzamido)benzoic acid (620 mg, 91%) as a yellow oily liquid.

[0050] 1 H NMR (400 MHz, Chloroform- d ) δ 7.79 (m, 1H), 7.34-7.27 (m, 3H), 7.25-7.16 (m, 3H), 7.01 (m, 1H), 3.51 (s, 3H).

[0051] LCMS: (ESI, m / z): [M+1] + = 274....

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PUM

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Abstract

The invention discloses a synthesis method of an aromatic amine carboxylic acid derivative. The synthesis method comprises the following steps of: S1, preparing a compound III of which the structural formula is shown in the specification; S2, preparing a compound IV of which the structural formula is shown in the specifications; S3, preparing a compound V of which the structural formula is shown in the specifications; S4, preparing a compound VI of which the structural formula is shown in the specifications; and S5, preparing a compound VIII of which the structural formula is shown in the specifications. With the synthesis method adopted, a brand new aromatic amine carboxylic acid derivative is designed and synthesized; and resources are provided for discovering better pest control drugs with higher cost performance. The raw materials adopted by the method are easy to obtain; the route design is reasonable; and industrialization is easy to realize.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis of aromatic amide derivatives, and in particular relates to a synthesis method of aromatic amine carboxylic acid derivatives. Background technique [0002] The prior art separately discloses methods for synthesizing various amide derivatives having agricultural pest control effects. Although the existing synthesis methods and types of amide derivatives have been disclosed in previous patents, the types disclosed are not comprehensive enough, and there are many deficiencies in the preparation methods, yields, routes, etc. Contents of the invention [0003] The purpose of the present invention is to design and disclose many new aromatic amine carboxylic acid derivatives with pest control effect and provide a synthetic method of aromatic amine carboxylic acid derivatives to solve the problems raised in the above-mentioned background technology. [0004] The present invention provides a kind...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/14C07C231/24C07C237/42C07C231/02C07C231/12C07C233/81
CPCC07C231/14C07C231/24C07C231/02C07C231/12C07C233/81C07C237/42
Inventor 曲文岩
Owner BEIJING YINONG BIOTECHNOLOGY CO LTD
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