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2-amino-4-acetamino anisole synthesis process

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

Inactive Publication Date: 2016-02-24
安徽奥瑞化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] 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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  • 2-amino-4-acetamino anisole synthesis process
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  • 2-amino-4-acetamino anisole synthesis process

Examples

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Embodiment 1

[0051] Weigh 1000g of 2,4-dinitrochlorobenzene (I), 1500g of methanol and 25g of PEG4000 into a four-neck flask, raise the temperature to 60°C, and stir; add 198g of sodium hydroxide and sodium hydroxide in batches within 2.5 to 3.0 hours After adding, keep warm, and the reaction ends. Methanol was recovered by distillation and washed with water to obtain 950.8 g (99%) of 2,4-dinitroanisole (II), with a yield of 96.9%.

[0052] The NMR data of 2,4-dinitroanisole (II) are as follows: 1 HNMR (500MHz, CDCl 3 ): δ8.83(d,1H), 8.4~8.5(dd,1H), 8.72(d,1H), 3.78(s,3H).

Embodiment 2

[0054] Put 950.8g (99%) 2,4-dinitroanisole (II), 3803.2g methanol and 0.95g Raney-Ni catalyst into a four-necked flask, the system pH=8, the temperature rose to 70°C, and the Into 1.0MPa hydrogen, the reaction is complete. The catalyst Raney-Ni was recovered by filtration. The HPLC purity of the active ingredient 2,4-diaminoanisole (III) in the mother liquor was 99.3%, and the conversion rate was 100%. The mother liquor was directly used for the acylation reaction without treatment.

[0055] Add 189.6g of ammonium bicarbonate to the above mother liquor, cool to -5°C, add 489.7g of acetic anhydride, after the addition is complete, raise the temperature to 5°C and keep warm until the reaction is complete. Distill 3042g of methanol, add water to the residue, cool and crystallize, and suction filter to obtain 770.2g (HPLC purity 99.5%) 2-amino-4-acetamidoanisole (IV), 2,4-diacetamidophenyl The amount of methyl ether generated is below 1% (measured by HPLC), and the total yield of...

Embodiment 3

[0058] Weigh 1,000g of 2,4-dinitrochlorobenzene (I), 2,500g of methanol, and 15g of benzyltriethylammonium chloride into a four-neck flask, raise the temperature to 70°C, and stir; within 2.5 to 3.0 hours, batch Add 196g of sodium hydroxide, add sodium hydroxide, keep warm, and the reaction ends. Methanol was recovered by distillation and washed with water to obtain 928.8 g (HPLC purity 99.2%) of 2,4-dinitroanisole (II), with a yield of 94.8%.

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Abstract

The invention discloses a 2-amino-4-acetamino anisole synthesis process. The process comprises the following steps that in methyl alcohol, 2,4-diaminobenzene methyl ether (III) and acetic anhydride are subjected to an acylation reaction as follows under the effect of an acid-binding agent to obtain 2-amino-4-acetamino anisole (IV), wherein the mole ratio of the acid-binding agent to the 2,4-diaminobenzene methyl ether is 0.3:1-0.6:1. The synthesis process is low in energy consumption, low in cost, small in amount of solid waste and liquid waste, free of pollution, environmentally friendly, easy to operate, mild in reaction condition and high in industrial safety coefficient, the target compound yield is 86% or above (based on initial reaction raw materials), the HPLC purity is 99.0% or above, and the target compound is high in yield, good in quality, and 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) [also known as 3-amino-4-methoxyacetanilide, commonly known as reduction, It is an important intermediate for the preparation of Disperse Blue 79, Disperse Blue 301 and Disperse Blue 270. The early production process of 2-amino-4-acetamidoanisole (IV) was based on p-aminoanisole (V) as the main starting material, and 2-aminoanisole was prepared by acetylation, mixed acid nitration, and iron powder reduction. -4-acetamidoanisole (IV), its chemical reaction formula is as follows: [0003] [0004] The process conditions are mature, the yield of product 2-amino-4-acetamidoanisole (IV) is stable, and the quality is reliable. However, a large amount of iron powder is used in the iron powder reduction step process. After the reaction is completed, a large ...

Claims

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Application Information

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IPC IPC(8): C07C233/43C07C231/02
CPCC07C231/02
Inventor 李新源
Owner 安徽奥瑞化工有限公司
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