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Method for preparing 2-amino-4-acetamido anisole

A technology of acetamidoanisole and dinitroanisole, which is applied in the field of preparation of 2-amino-4-acetamidoanisole, can solve the problem of high equipment safety requirements, serious environmental pollution and harsh operating conditions To achieve the effect of safe and easy to control the reaction process, low equipment requirements, and increase product content

Active Publication Date: 2015-09-23
上海惠仁(夏邑)制药有限公司
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Problems solved by technology

[0003] The existing methods for preparing 2-amino-4-acetamidoanisole have serious environmental pollution, large consumption of reagents, high requirements for equipment safety, and high cost. Disadvantages such as high and side effects
For example: when preparing the intermediate product 2,4-diaminoanisole of 2-amino-4-acetamidoanisole, the catalytic hydrogenation method is usually used in the literature to realize, and this method must be carried out in an autoclave. Harsh, high requirements for equipment safety, not suitable for large-scale industrial production; Hao Yanxia et al. , 30(6):682) the synthetic method used produces more strong acid waste liquid, which pollutes the environment; the domestic patent (application number: 201310308426.9) uses Raney nickel as the catalyst, although it has a good catalytic effect, but due to its presence in the air Easy to ignite spontaneously, there is a big safety hazard

Method used

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  • Method for preparing 2-amino-4-acetamido anisole

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 100kg of 2,4-dinitroanisole, 50kg of hydrazine hydrate with a mass percentage of 80%, 10kg of iron acetylacetonate, and 500kg of methanol into a reaction flask with a condensing reflux device, and control the temperature at 65°C for 4 hours. , filtered and recovered the magnetic Fe 3 o 4 After powdering, 2,4-diaminoanisole-methanol mixture is obtained; then the obtained 2,4-diaminoanisole-methanol mixture is placed in a reaction bottle, and the ice bath (0 ° C ~ 5 ° C) conditions Add 75 kg of acetic anhydride dropwise while stirring, and control the dropwise addition within 40 minutes, and continue to keep the ice bath for 30 minutes under stirring, and recover methanol by distillation under reduced pressure, then filter and dry to obtain 2-amino-4-acetamidobenzene 89.5kg product of methyl ether (content: 99.7%, yield: 98.5%).

Embodiment 2

[0019] Add 350kg of 2,4-dinitroanisole, 250kg of hydrazine hydrate with a mass percentage of 80%, 52.5kg of nickel acetylacetonate, and 1750kg of tetrahydrofuran into a reaction flask with a condensing reflux device, and control the temperature to react at 70°C After 3 hours of filtration, the 2,4-diaminoanisole-tetrahydrofuran mixture was obtained; then the obtained 2,4-diaminoanisole-tetrahydrofuran mixture was placed in a reaction flask, and placed in an ice bath (0°C~5°C 280kg of acetic anhydride was added dropwise while stirring under the condition of stirring, and the dropwise addition was completed within 1 hour, and the ice bath was kept for 40 minutes under stirring, and tetrahydrofuran was recovered by distillation under reduced pressure, and then filtered and dried to obtain 2-amino-4-acetyl Anisoline 312kg product (content: 99.5%, yield: 98%).

Embodiment 3

[0021] Add 200kg of 2,4-dinitroanisole, 140kg of hydrazine hydrate with a mass percentage of 80%, 24kg of ruthenium acetylacetonate, and 700kg of ethanol in sequence in a reaction flask with a reflux device, and control the temperature at 70°C for 4 hours. After filtration, the 2,4-diaminoanisole-ethanol mixture was obtained; then the obtained 2,4-diaminoanisole-ethanol mixture was placed in a reaction flask, and placed in an ice bath (0°C~5°C) Add 180kg of acetic anhydride dropwise while stirring under the conditions, control the dropwise addition within 50min, and keep the ice bath condition under stirring for 40min, recover ethanol by distillation under reduced pressure, then obtain 2-amino-4-acetyl after filtration and drying Anisoline 178.5kg product (content: 99.2%, yield: 98.2%).

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Abstract

The invention discloses a method for preparing 2-amino-4-acetamido anisole, and belongs to the field of organic chemistry synthesis. 2,4-dinitrobenzene methyl ether is adopted as raw materials, reduction is carried out through hydrazine hydrate under the action of diacetone catalysts to obtain mixed liquor of 2,4-dinitrobenzene methyl ether-solvents, then after acetylation is carried out under the action of acetic anhydride, reduced pressure distillation and recycling are carried out on the solvents, and the product of 2-amino-4-acetamido anisole is obtained after filtering and drying. The method has the advantages that the yield is high, the effect is good, environmental protection is achieved, the requirement for equipment is not high, and the method is easy and convenient to operate, and the good industrialized application value is achieved.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a preparation method of 2-amino-4-acetamidoanisole. technical background [0002] 2-Amino-4-acetamidoanisole is an important intermediate for the preparation of dark (blue) varieties, and can be used to prepare C.I. Disperse Blue 79, C.I. Disperse Blue 301, C.I. Disperse Blue 58 and other disperse blue series dyes and The coupling component of deep blue HGL has stable quality, high emission intensity, excellent application performance of dyes, great market demand and good market prospect. [0003] The existing methods for preparing 2-amino-4-acetamidoanisole have disadvantages such as serious environmental pollution, large consumption of reagents, high requirements for equipment safety, high cost and many side reactions. For example: when preparing the intermediate product 2,4-diaminoanisole of 2-amino-4-acetamidoanisole, the catalytic hydrogenation method i...

Claims

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Application Information

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IPC IPC(8): C07C233/43C07C231/02
Inventor 胡孝伦杨勇王建莉赵萍萍郝家金李义波
Owner 上海惠仁(夏邑)制药有限公司
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