Synthesis process of 2-amino-4-acetamino anisole

A technology for 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 industrialized production, low industrial safety factor, etc., and achieves reduction of side effects. The probability of product formation, the reduction of dosage, the effect of high industrial safety factor

Inactive Publication Date: 2015-07-22
SHANGHAI ZONGXING CHEM TECH CO LTD
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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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  • Synthesis process of 2-amino-4-acetamino anisole
  • Synthesis process of 2-amino-4-acetamino anisole
  • Synthesis process of 2-amino-4-acetamino anisole

Examples

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Embodiment 1

[0051] Weigh 1000g of 2,4-dinitrochlorobenzene (I), 1500g of methanol into a four-neck flask, 25g of PEG4000, heat up to 60°C, stir; add 198g of sodium hydroxide in batches within 2.5 to 3.0 hours, hydrogen Add sodium oxide, 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, the system pH=8, the temperature was raised to 70°C, and 1.0MPa hydrogen gas was continuously introduced, 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 yiel...

Embodiment 3

[0058] Weigh 1000g of 2,4-dinitrochlorobenzene (I), 2500g of methanol into a four-neck flask, 15g of benzyltriethylammonium chloride, heat up to 70°C, and stir; within 2.5 to 3.0 hours, divide Add 196g of sodium hydroxide in batches, 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 synthesis process of 2-amino-4-acetamino anisole. The synthesis process comprises the following steps: in methanol, under the action of an acid-binding agent, 2,4-diaminoanisole (III) and acetic anhydride are subject to acylation reaction shown in the description to obtain 2-amino-4-acetamino anisole (IV), wherein the molar ratio of the acid-binding agent to 2,4-diaminoanisole is (0.3 : 1)-(0.6 : 1). The synthesis process is low in energy consumption and cost, less in waste solids and waste liquid, environment-friendly, simple in operation, mild in reaction condition and high in industrial safety factor, the yield of the target compound is above 86% (counting according to original reaction raw materials), the HPLC purity is above 99.0%, the target compound is high in yield and good in quality, and the synthesis process is more suitable for 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, ], 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/43C07C231/02
CPCY02P20/584
Inventor 李新源
Owner SHANGHAI ZONGXING CHEM TECH CO LTD
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