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Preparation method of 2-(3-amino-4-chlorobenzoyl)benzoic acid

A technology of chlorobenzoyl and nitrobenzoyl, which is applied in the field of preparation of 2-benzoic acid, can solve the problems of unsuitability for industrial production, unsafe process, long reaction time, etc., and achieve low cost, high purity, and reduced Effects of Response Costs

Active Publication Date: 2018-04-20
KINGCHEM LIAONING CHEMICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the process is cumbersome to operate, the reaction time is long, nearly 8 hours, and copper-containing wastewater is produced.
Wang Zhonghan (Chlorthalidone Synthesis Process Improvement [J]. Pharmaceutical Industry, 1982, 04: 20-21) Prepared by catalytic reaction of 2-(3-nitro-4-chlorobenzoyl)benzoic acid, hydrazine hydrate and active nickel 2-(3-amino-4-chlorobenzoyl)benzoic acid, the total yield is greater than 91%, but the process is unsafe, and the reaction time is as long as 16h, so it is not suitable for industrial production
[0004] This shows that the method for preparing 2-(3-amino-4-chlorobenzoyl)benzoic acid provided in the prior art generally has the defect that the reaction time is too long

Method used

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  • Preparation method of 2-(3-amino-4-chlorobenzoyl)benzoic acid
  • Preparation method of 2-(3-amino-4-chlorobenzoyl)benzoic acid
  • Preparation method of 2-(3-amino-4-chlorobenzoyl)benzoic acid

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[0024] The invention provides a kind of preparation method of 2-(3-amino-4-chlorobenzoyl)benzoic acid, comprising the following steps:

[0025] Mix 2-(4-chloro-3-nitrobenzoyl)benzoic acid, Raney nickel and an organic solvent, and carry out a hydrogenation reaction under a hydrogen atmosphere to obtain 2-(3-amino-4-chlorobenzoyl )benzoic acid;

[0026] The time for the hydrogenation reaction is 1 to 5 hours.

[0027] In the present invention, the raw materials used in the preparation method can all be commercially available raw materials well known to those skilled in the art, and will not be described in detail below.

[0028] The invention mixes 2-(4-chloro-3-nitrobenzoyl)benzoic acid, Raney nickel and an organic solvent to obtain a raw material mixture. The present invention has no special requirements on the mixing method, as long as all components can be mixed evenly. The present invention uses commercially available Raney nickel, and the Raney nickel product contains 2...

Embodiment 1

[0047]Add 100 g (0.33 mol) of 2-(3-nitro-4-chlorobenzoyl)benzoic acid, 600 g of ethyl acetate, and 10 g of Raney nickel (20% water content) into a 1L stainless steel autoclave, and seal the kettle after adding , start stirring, nitrogen replacement three times, pass hydrogen to 1.0MPa, heat up to 35°C for reaction, when the hydrogen pressure is 98% detected by HPLC, yield 95%, melting point 179~183°C.

[0048] The HPLC detection result of described 2-(3-amino-4-chlorobenzoyl) benzoic acid is as table 1 and figure 1 shown.

[0049] The HPLC detection result of 2-(3-amino-4-chlorobenzoyl)benzoic acid in the embodiment 1 of table 1

[0050]

[0051] The structure of the product was identified using nuclear magnetic resonance, and the results were as follows figure 2 shown, combined with figure 2 It can be seen that the obtained identification data are as follows:

[0052] 1 H NMR (DMSO-d6,400MHz)δ13.233(s,1H),8.041-8.060(d,1H),7.773-7.792(t,1H),7.716-7.737(m,1H),7.456-7...

Embodiment 2

[0054] In 1L stainless steel autoclave, add 2-(3-nitro-4-chlorobenzoyl) benzoic acid 100g (0.33mol), ethyl acetate 600g, the Raney nickel 10g (water content 20%) that embodiment 1 obtains and fresh Raney nickel 2g (water content 20%), after the addition, seal the kettle, start stirring, replace with nitrogen three times, pass hydrogen to the pressure of 2.0MPa, heat up to 40°C for reaction, when the hydrogen pressure is 98% detected by HPLC, yield 96%, melting point 179~183°C.

[0055] The HPLC detection result of described 2-(3-amino-4-chlorobenzoyl) benzoic acid is as table 2 and image 3 shown.

[0056] The HPLC detection result of 2-(3-amino-4-chlorobenzoyl)benzoic acid in the embodiment 2 of table 2

[0057]

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Abstract

The present invention provides a preparation method of 2-(3-amino-4-chlorobenzoyl) benzoic acid. The method is as follows: 2-(4-chloro-3-nitrobenzoyl) benzoic acid, Raney nickel and an organic solventare mixed for hydrogenation under a hydrogen atmosphere to obtain 2-(3-amino-4-chlorobenzoyl) benzoic acid; and the hydrogenation time is 1 to 5 hours. In the method, the Raney nickel is used as a catalyst to catalyze the reaction of the 2-(4-chloro-3-nitrobenzoyl) benzoic acid with hydrogen, and the choice of the reaction system achieves an excellent cooperation between the catalyst and a reaction raw material. The reaction takes less time. The method can successfully obtain the 2-(3-amino-4-chlorobenzoyl) benzoic acid, and the reaction time can be shortened to 2 to 3 hours; furthermore, themethod has the advantages of mild reaction conditions, high target product purity, high yield, low cost, friendliness to the environment, and suitability for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2-(3-amino-4-chlorobenzoyl)benzoic acid. Background technique [0002] 2-(3-Amino-4-chlorobenzoyl)benzoic acid is an important intermediate in the synthesis of thilones. Thiketones are mainly used to treat hemorrhagic heart failure, liver cirrhosis ascites, nephropathy neutralization, acute and chronic pneumonia edema, early acute and chronic renal failure, sodium retention caused by adrenal corticosteroid and estrogen therapy. It can be used alone or in combination with other antihypertensive drugs, mainly for the treatment of essential hypertension. [0003] Patent publication number is that the Chinese patent of CN105906521A discloses a kind of preparation method of 2-(3-amino-4-chlorobenzoyl) benzoic acid, by 2-(3-nitro-4-chlorobenzoyl) benzoic acid After reacting with cuprous chloride and potassium iodide, 2-(3-amino-4-chlorobenzoyl)benzoi...

Claims

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Application Information

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IPC IPC(8): C07C229/52C07C227/04
CPCC07C227/04C07C229/52
Inventor 王安钢李艳凤姜志鹏高恩松胡志山马莹刘强
Owner KINGCHEM LIAONING CHEMICAL CO LTD
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