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Process for the preparation of quinmerac

A technology of quinolincarboxylic acid and chlorobenzonitrile, which is applied in botany equipment and methods, organic chemistry, animal husbandry, etc., and can solve problems such as low yield and waste

Active Publication Date: 2021-02-26
ADAMA AGAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Oxidation leads to relatively low yields and a lot of waste

Method used

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  • Process for the preparation of quinmerac
  • Process for the preparation of quinmerac
  • Process for the preparation of quinmerac

Examples

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preparation example Construction

[0024] Preparation of quinclorac:

[0025] The invention provides a kind of method preparing the quinclorac represented by following formula (I):

[0026]

[0027] The method comprises making 2-amino-6-chlorobenzonitrile represented by the following formula (II):

[0028]

[0029] Reacts with methacrolein in the presence of acids and oxidizing agents.

[0030] In one embodiment of the invention, said acid is selected from sulfuric acid and hydrochloric acid.

[0031] In a specific embodiment, the acid is sulfuric acid.

[0032] In one embodiment of the method of the invention, the molar ratio between the compound of formula (II) and the acid is from about 1:1 to about 1:50. In another embodiment, the molar ratio between the compound of formula (II) and the acid is from about 1:1 to about 1:25.

[0033] In a particular embodiment, the molar ratio between the compound of formula (II) and the acid is about 1:10.

[0034] In another specific embodiment, the molar rati...

Embodiment

[0066]Raw material consumption on 2.0g scale

[0067] name mw equivalent g / batch (ml / batch) 2-Amino-6-chlorobenzonitrile 152.58 1.0 2.00g methacrolein 70.09 2.0 1.84g boric acid 61.83 1.0 0.81g Concentrated H 2 SO 4

98.08 10.0 12.86g FeSO 4 ·7H 2 o

278.01 0.2 0.73g Nitrobenzene 123.11 2.0 2.70ml water - - 4.80ml

[0068] All reagents including 2-amino-6-chlorobenzonitrile were purchased from Sigma-Aldrich.

[0069] general method

[0070] 2.00g (13.1mmol) 2-amino-6-chlorobenzonitrile, 0.81g (13.1mmol) boric acid, 12.86g (131.1mmol) concentrated H 2 SO 4 , 0.73g (2.6mmol) FeSO 4 ·7H 2 O. Add 2.16ml (1.84g; 26.2mmol) methacrolein dropwise to a suspension of 2.70ml (26.2mmol) nitrobenzene and 4.80ml water. The reaction mixture was then stirred at 130°C for 6 hours. The reaction mixture was cooled and poured into 50 g of ice water. The precipitate was filtered off, and the pH of the filt...

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Abstract

It is an object of the present invention to provide a novel and advantageous process for commercially preparing quinmerac.

Description

technical field [0001] The present invention relates to an improved process for the preparation of 7-chloro-3-methyl-8-quinolinic acid known as quinmerac. Background technique [0002] The quinolinic acid whose chemical name is 7-chloro-3-methyl-8-quinolinic acid is represented by the following formula (I). [0003] [0004] Quinorac is a synthetic plant auxin. It induces the formation of 1-aminocyclopropane-1-carboxylic acid, leading to the formation of ethylene, which induces the formation of abscisic acid (K. Grossmann & F. Scheltrup, Proc. Br. CropProt. Conf-Weeds, 1995, 1, 393). [0005] The use of quinclorac as a herbicide is described in European patent EP104389. [0006] The synthesis of quinolinecarboxylic acids by subjecting anthranilic acid to a Skraup cyclization is known (Monatsh 21981, 518). However, the yields were generally low, especially in the case of 8-quinolinecarboxylic acids, due to partial decarboxylation under the reaction conditions. [0007]...

Claims

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Application Information

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IPC IPC(8): A01N43/42C07D215/16C07D215/18C07D215/48
CPCC07D215/48C07D215/06C07D215/18
Inventor A·亚科文O·特佐尔
Owner ADAMA AGAN
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