Process for synthesizing 2-amino-4-acetylaminoanisole

A technology of acetaminoanisole and diaminoanisole, which is applied in the field of preparation of organic compounds, can solve problems such as unstable yield and quality of target compounds, unsuitability for industrial production, and a large amount of waste solids and waste liquids. The effect of reducing the chance of by-product formation, reducing the dosage, and high industrial safety factor

Inactive Publication Date: 2018-07-20
张翔
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0022] The technical problem to be solved by the present invention is to overcome the high energy consumption, high cost, generation of a large amount of waste solid and waste liquid, serious environmental pollution, Complicated operation, harsh reaction conditions, low industrial safety factor, unstable yield and quality of the target compound, and inapplicability to industrialized production, etc., and a synthetic process for 2-amino-4-acetamidoanisole is provided

Method used

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  • Process for synthesizing 2-amino-4-acetylaminoanisole
  • Process for synthesizing 2-amino-4-acetylaminoanisole
  • Process for synthesizing 2-amino-4-acetylaminoanisole

Examples

Experimental program
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Effect test

Embodiment 1

[0055] Weigh 100g of 2,4-dinitrochlorobenzene (I), 200g of methanol, and 2.5g of PEG2000 into a four-neck flask, heat up to 60°C, and stir; add 20g of sodium hydroxide in batches within 2.5 to 3.0 hours, Add sodium hydroxide, keep warm, and the reaction ends. Methanol was recovered by distillation and washed with water to obtain 95 g (99%) of 2,4-dinitroanisole (II), with a yield of 96.1%.

[0056] The NMR data of 2,4-dinitroanisole (II) are as follows: 1 HNMR (500MHz, CDCl3): δ8.82 (d, 1H), 8.4-8.5 (dd, 1H), 8.73 (d, 1H), 3.77 (s, 3H).

Embodiment 2

[0058] Put 95g (HPLC purity 99.2%) 2,4-dinitroanisole (II), 380g methanol and 0.95g Pd / C catalyst into a four-necked flask, add 85.5g monoformic acid hydrazine salt, react at room temperature, and react complete. The catalyst Pd / C was recovered by filtration. The HPLC purity of the active ingredient 2,4-diaminoanisole (III) in the mother liquor was 99.1%, and the conversion rate was 100%. The mother liquor was directly used in the acylation reaction without treatment.

[0059] Add 19.0g of sodium carbonate to the above mother liquor, cool to -5°C, add 47.2g of acetic anhydride, after the addition is complete, raise the temperature to 5°C and keep warm until the reaction is complete. Distill 304g of methanol, add water to the residue, cool and crystallize, and suction filter to obtain 75.1g (HPLC purity 99.5%) 2-amino-4-acetamidoanisole (IV), 2,4-diacetamidobenzene The amount of methyl ether generated is below 1% (measured by HPLC), and the total yield of the two steps is 89.0...

Embodiment 3

[0062] Weigh 100g of 2,4-dinitrochlorobenzene (I), 150g of methanol, and 1.6g of benzyltriethylammonium chloride into a four-neck flask, heat up to 70°C, and stir; within 2.5 to 3.0 hours, Add 19.7g of sodium hydroxide in batches, after adding the sodium hydroxide, keep warm, and the reaction ends. Methanol was recovered by distillation and washed with water to obtain 92.8 g (HPLC purity 99.1%) of 2,4-dinitroanisole (II), with a yield of 93.9%.

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Abstract

The invention discloses a process for synthesizing 2-amino-4-acetylaminoanisole. The process comprises the steps of preparing 2,4-dinitroanisole from 2,4-dinitrochlorobenzene, which serves as a raw material, in methanol, in the presence of sodium hydroxide or potassium hydroxide, carrying out reduction in the presence of action of Pd/C catalyst by taking hydrazine monoformate as a hydrogen sourceso as to prepare a 2,4-diaminoanisole-methanol solution, and then, subjecting 2,4-diaminoanisole and acetic anhydride to a partial acylation reaction in the presence of an acid binding agent, therebypreparing the 2-amino-4-acetylaminoanisole. According to the process disclosed by the invention, the energy consumption is low, the cost is low, the volume of solid waste and waste liquid is small, the process is environmentally friendly, the operation is simple, the reaction conditions are mild, the industrial safety coefficient is big, the total yield of a target compound is 85% or more (by initial reactants), the HPLC purity is 99.0% or more, and the target compound is high in yield and good in quality, so that the process is more applicable to industrial production.

Description

technical field [0001] The invention relates to a preparation method of an organic compound, in particular to a synthesis process of 2-amino-4-acetamidoanisole. Background technique [0002] 2-amino-4-acetamidoanisole (IV) is an important intermediate for the preparation of azo dyes such as disperse blue 79, disperse blue 270, disperse blue 301, etc. The early production process of 2-amino-4-acetamidoanisole (IV) was based on p-aminoanisole (V) as the main starting material, through acetylation, mixed acid (nitric acid and sulfuric acid) nitration, iron powder reduction Obtain 2-amino-4-acetamidoanisole (IV), its chemical reaction formula is as follows: [0003] [0004] The process conditions are mature, the product 2-amino-4-acetamidoanisole (IV) yield is stable, and the quality is reliable. However, in the iron powder reduction step process, a large amount of iron powder is used. After the reaction, a large amount of heat is required. Water washes the organic matter ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/37C07C213/02C07C217/84C07C231/02C07C233/43
CPCC07C201/12C07C213/02C07C231/02C07C205/37C07C217/84C07C233/43
Inventor 张翔
Owner 张翔
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