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Synthesis method and application of 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide

A synthetic method, the technology of chlorinated biphenyls, applied in the field of pesticide fungicides, can solve the problem of low nicotinamide yield and achieve the effect of simple operation steps

Active Publication Date: 2020-04-21
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The purpose of the present invention is to provide a kind of synthetic method of 2-hydroxyl-N-(4'-chlorobiphenyl-2-yl)nicotinamide, to solve the existing 2-hydroxyl-N-(4 '-chlorobiphenyl-2-yl) nicotinamide yield low problem;

Method used

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  • Synthesis method and application of 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide
  • Synthesis method and application of 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide
  • Synthesis method and application of 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 The synthetic method of 2-hydroxyl-N-(4'-chlorobiphenyl-2-yl) nicotinamide

[0050] Using 2-chloronicotinic acid and 4'-chloro-2-aminobiphenyl as raw materials, react with catalyst 3-nitrophenylboronic acid in toluene solution at 120°C to generate 2-hydroxy-N-(4'-chlorobiphenyl- 2-yl) nicotinamide, the specific synthetic route is as follows:

[0051]

[0052] Step 1): Measure 1.56kg (ie 10mol) of 2-chloronicotinic acid, 1.02kg (ie 5mol) of 4'-chloro-2-aminobiphenyl, and 0.42kg (ie 2.5mol) of 3-nitrobenzene Boric acid, spare;

[0053] Measure 30L of toluene, add 2-chloronicotinic acid to toluene, stir to dissolve at room temperature, add 4'-chloro-2-aminobiphenyl, stir and mix, then add 3-nitrophenylboronic acid, heat to 120°C, And after keeping at 120°C for 10 hours, the solution B was prepared, and the temperature of the solution B was naturally cooled to room temperature;

[0054] Step 2): Add 30L of saturated aqueous sodium bicarbonate solution to solut...

Embodiment 2-9

[0060] Example 2-9 The synthetic method of 2-hydroxyl-N-(4'-chlorobiphenyl-2-yl)nicotinamide

[0061] Examples 2-9 are respectively the synthesis method of 2-hydroxy-N-(4'-chlorobiphenyl-2-yl) nicotinamide, the synthesis method is the same as that of Example 1, the difference is that the above-mentioned 2-hydroxy- The various process parameters in the N-(4'-chlorobiphenyl-2-yl) nicotinamide process are different, see Table 1 for details:

[0062] List of various process parameters in Table 1 Embodiment 2-9

[0063]

[0064] The following is the refining method of 2-hydroxyl-N-(4'-chlorobiphenyl-2-yl) nicotinamide synthesized in Example 2-9, the refining method is the same as in Example 1, the difference is that the above-mentioned 2 -Hydroxy-N-(4'-chlorobiphenyl-2-yl) nicotinamide process conditions are different, see Table 2 for details:

[0065] List of various refining process conditions in table 2 embodiment 2-9

[0066]

Embodiment 10

[0067] Example 10 Application of 2-hydroxyl-N-(4'-chlorobiphenyl-2-yl)nicotinamide

[0068] 2-Hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide fine product prepared in Example 1, as a standard reference substance, by comparing 2-hydroxy-N-(4'-chlorobiphenyl-2 - base) liquid phase diagram of nicotinamide and boscalid to detect the presence of 2-hydroxy-N-(4'-chlorobiphenyl-2-yl) nicotinamide and The amount of the content can realize the monitoring of the synthesis process of boscalid and the detection of the quality of boscalid products.

[0069] Monitoring the synthesis of boscalid:

[0070] Producing boscalid according to the prior art, p-chlorobromobenzene makes p-chlorophenylboronic acid through Grignard reaction, then with o-chloronitrobenzene in catalyst MS-Pd, anhydrous potassium carbonate and tetrabutylammonium bromide ( In the presence of TBAB), a Suzuki reaction occurs at 120°C in DMF to generate 2-(4-chlorophenyl)nitrobenzene; then 2-(4-chlorophenyl)aniline is obtain...

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Abstract

The invention discloses a synthesis method of 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide, and belongs to the field of pesticide bactericides. The 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamideis prepared from 2-chloronicotinic acid and 4'-chloro-2-aminobiphenyl as raw materials in the presence of at least one catalyst of zirconium chloride, n-butylstannic acid, boric acid, 3, 4, 5-trifluorophenylboronic acid and 3-nitrophenylboronic acid. The invention also discloses an application of the 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide prepared by the synthesis method in monitoring the generation condition of boscalid in the boscalid production process and detecting the content of boscalid. The yield of the 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide synthesized by the synthesis method is greater than or equal to 50.48%, the problem of low yield is solved, and the synthesized product is used for monitoring the generation condition of boscalid in the boscalid production process and detecting the content of boscalid.

Description

technical field [0001] The invention belongs to the field of pesticide fungicides, in particular to a synthesis method and application of 2-hydroxy-N-(4'-chlorobiphenyl-2-yl)nicotinamide. Background technique [0002] Boscalid is a new type of nicotinamide fungicide developed by BASF, Germany. It is mainly used to prevent and control powdery mildew, gray mold, and various rot diseases. [0003] Boscalid is a succinate coenzyme Q reductase inhibitor in the mitochondrial respiratory chain, which has a strong inhibitory ability to spore germination and has no cross-resistance with other fungicides. [0004] In the existing technical scheme, the synthesis of boscalid mainly adopts two synthetic methods: [0005] 1. a kind of synthetic method is, p-chlorobromobenzene makes p-chlorophenylboronic acid through Grignard reaction, and then with o-chloronitrobenzene in catalyst MS-Pd, anhydrous potassium carbonate and tetrabutylammonium bromide (TBAB) In the presence of DMF, a Suzuki...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82G01N30/88
CPCC07D213/82G01N30/88G01N2030/8845
Inventor 张越谢晓辉
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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