Method for preparing 5-methyl carboxylate-6-benzoltriazolylmethoxy

A technology of methoxybenzene and methyl carboxylate, applied in the field of organic compound synthesis, can solve problems such as unseen compound research reports, and achieve the effects of easy industrial production, good practicability, good economic benefits and social benefits

Inactive Publication Date: 2012-04-04
苏州诚和医药化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] 5-Carboxylic acid (methyl ester)-6-methoxybenzotriazole is an important intermediate in the synthesis of functional colorants for photosensitive materials. There is no research report on this compound at home and abroad

Method used

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  • Method for preparing 5-methyl carboxylate-6-benzoltriazolylmethoxy
  • Method for preparing 5-methyl carboxylate-6-benzoltriazolylmethoxy
  • Method for preparing 5-methyl carboxylate-6-benzoltriazolylmethoxy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In the dry reaction flask, add 72.5g (0.4mol) methyl 2-methoxy-4-aminobenzoate, 140mL glacial acetic acid, 126g (1.23mol) acetic anhydride, stir to dissolve, heat up to 40°C, stir for 0.5 h, add 48ml (d=1.49) of nitric acid dropwise, stir at 40°C for 2h, after the reaction is complete, pour the reaction solution into 600ml of methanol containing 0.4mol of sulfuric acid, stir, add 1600g of ice water, precipitate crystals, filter, Dry to obtain 55.2 g of methyl 2-methoxy-4-amino-5-nitrobenzoate, mp=213.1~214.6°C.

[0020] In the reaction kettle, add 2-methoxy-4-amino-5-nitrobenzoic acid methyl ester 555g (2.45mol), 30g Raney nickel, 2500mL methanol, at 50 ℃, 0.6Mpa hydrogen pressure, hydrogen Hydrogenation until the theoretical amount, the reaction is complete, cooled and filtered, washed with methanol. The solvent was recovered from the filtrate under reduced pressure. Cool to precipitate crystals, wash with methanol, and dry at 50°C to obtain 305g of methyl 2-methoxy-...

Embodiment 2

[0023] In the dry reaction bottle, add 72.5g (0.4mol) methyl 2-methoxy-4-aminobenzoate, 160mL glacial acetic acid, 138g (1.35mol) acetic anhydride, stir to dissolve, heat up to 40°C, stir for 0.5 h, add 52ml (d=1.49) of nitric acid dropwise, stir at 40°C for 2h, after the reaction is complete, pour the reaction solution into 600ml of methanol containing 0.4mol of sulfuric acid, stir, add 1600g of ice water, precipitate crystals, filter, After drying, 56.3 g of methyl 2-methoxy-4-amino-5-nitrobenzoate was obtained, mp=213.6~214.8°C.

[0024] In the reaction kettle, add 2-methoxy-4-amino-5-nitrobenzoic acid methyl ester 555g (2.45mol), 30g Raney nickel, 2500mL methanol, at 50 ℃, 0.8Mpa hydrogen pressure, pass Hydrogen hydrogenation until the theoretical amount, the reaction is complete, cooled and filtered, washed with methanol. The solvent was recovered from the filtrate under reduced pressure. Cool to precipitate crystals, wash with methanol, and dry at 50°C to obtain 312g o...

Embodiment 3

[0027] In a dry reaction flask, add 1mol 2-methoxy-4-aminobenzoic acid methyl ester, 4mol glacial acetic acid, 3.5mol acetic anhydride, stir to dissolve, heat up to 40°C, stir for 0.5h, add dropwise 2mol nitric acid (d = 1.49) dropwise, stirred at 40°C for 2h, and the reaction was completed, the reaction solution was poured into 1.5L of sulfuric acid-containing methanol (1mol / 1500ml), under stirring, an appropriate amount of ice water was added until crystals were precipitated, filtered, and dried to obtain 2 -Methoxy-4-amino-5-nitrobenzoic acid methyl ester, mp=213.1~214.6°C.

[0028] In the reaction kettle, add 450g of 2-methoxy-4-amino-5-nitrobenzoic acid methyl ester, 30g of Raney nickel, 1.8L of methanol, and hydrogenate at 50°C and 0.6Mpa hydrogen pressure until the theoretical When the reaction is complete, cool, filter, and wash with methanol. The solvent was recovered from the filtrate under reduced pressure. Cool to precipitate crystals, wash with methanol, and dry...

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Abstract

The invention discloses a method for preparing 5-methyl carboxylate-6-benzoltriazolylmethoxy. The method comprises the following steps of taking 2-methoxyl-4-aminobenzoate as a raw material, adding acetic anhydride and glacial acetic acid with a dissolved quantity and concentrated nitric acid with a nitration quantity in the raw material, performing a nitration reaction to prepare an intermediate of 2-methoxyl-4-amino-5-nitrobenzoate; taking 2-methoxyl-4-amino-5-nitrobenzoate as a raw material, adding methanol with a dissolved quantity and Raney nickel with a catalytic amount, controlling the pressure at 0.5-0.8 Mpa, putting hydrogen into the mixture, performing a hydrogenation reaction, pouring methanol aqueous solution containing sulfuric acid into the mixture, adding ices to separate out crystals, filtering and drying the crystal to obtain the intermediate 2-methoxyl-4,5-diaminobenzoate; adding the 2-methoxyl-4,5-diaminobenzoate in concentrated hydrochloric acid, adding sodium nitrite solution in the mixture drop by drop at a temperature of 0-5 DEG C, after the adding of the sodium nitrite solution is finished, heating the mixture to 30-35 DEG C and agitating the mixture for 1-2 hours; cooling and filtering the mixture, obtaining solid; washing the solid with methylene dichloride and water in sequence, obtaining the 5-methyl carboxylate-6-benzoltriazolylmethoxy. According to the method provided by the invention, the raw materials are easy to get, the operation is simple, the cost is low, the industrialization production is easy to realize, the product yield is high and more than 80%, therefore, the method has a good practicability and can produce good economic benefit and social benefit.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a method for preparing methyl 5-carboxylate-6-methoxybenzotriazole. Background technique [0002] 5-Carboxylic acid (methyl ester)-6-methoxybenzotriazole is an important intermediate in the synthesis of functional colorants for photosensitive materials. There is no research report on this compound at home and abroad. Contents of the invention [0003] Purpose of the invention: for the deficiencies in the prior art, the purpose of the present invention is to provide a method for preparing methyl 5-carboxylate-6-methoxybenzotriazole, so that it has raw materials that are easy to get, The method has the advantages of simple process, high product yield, convenient industrial production and the like. [0004] Technical solution: In order to realize the above-mentioned purpose of the invention, the technical solution adopted in the present invention is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/18
Inventor 王利明夏秋景陈浩
Owner 苏州诚和医药化学有限公司
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