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3-ethoxy-4-methoxy benzonitrile preparing method

A technology of methoxybenzonitrile and methoxybenzaldehyde, which is applied in the field of preparation of 3-ethoxy-4-methoxybenzonitrile, can solve the problems of high risk factor, high cost, large pollution and the like, and achieves Low environmental pollution, low production cost and easy post-processing

Inactive Publication Date: 2015-12-23
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to overcome the defects of high cost, high pollution and high risk factor in the prior art, the object of the present invention is to provide a 3-ethoxy-4-methanol with low cost, mild reaction conditions, easy post-treatment and environmental friendliness The preparation method of oxybenzonitrile, the content and yield of the product are also improved

Method used

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  • 3-ethoxy-4-methoxy benzonitrile preparing method
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  • 3-ethoxy-4-methoxy benzonitrile preparing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Put 0.5mol potassium carbonate, 0.5mol isovanillin and 100ml DMF into the reaction flask, stir and heat to 80°C, then slowly add 0.6mol (1.2eq) of bromoethane dropwise, and keep warm until the reaction of the raw materials is completed. Dissolving, extracting, concentrating, and drying to obtain 0.5 mol of white solid 3-ethoxy-4-methoxybenzaldehyde, 1.2% moisture, 98.9% purity, and 98.8% yield.

[0024] Drop into ethanol in reaction flask, hydroxylamine hydrochloride 0.6mol (1.5eq), sodium hydroxide 0.6mol (1.5eq) and above-mentioned 3-ethoxy-4-methoxybenzaldehyde 0.4mol that make, be warming up to 30- 40°C, heat-retaining reaction until the reaction of the raw materials is complete, add water to precipitate the product, and drain to obtain off-white solid 3-ethoxy-4-methoxybenzaldehyde oxime, dry 0.382mol, moisture 0.62%, purity 95.3%, yield 94.9%.

[0025] Put 1.05mol (3.5eq) of acetic anhydride and 0.3mol of the 3-ethoxy-4-methoxybenzaldehyde oxime prepared above in...

Embodiment 2

[0028] Put 0.5mol of potassium carbonate, 0.5mol of isovanillin and 100ml of DMF into the reaction bottle, stir and heat to 90°C, slowly add 0.5mol (1.0eq) of bromoethane dropwise, and keep the reaction until the raw materials are reacted , extraction, concentration, and drying to obtain 0.502mo of white solid 3-ethoxy-4-methoxybenzaldehyde, 1.3% moisture, 99.7% purity, and 99.1% yield.

[0029] Drop into ethanol, hydroxylamine hydrochloride 0.4mol (1.0eq) in reaction bottle, sodium hydroxide 0.4mol (1.0eq), the above-mentioned 3-ethoxy-4-methoxybenzaldehyde 0.4mol that makes, be warming up to 30- 40°C, keep warm until the reaction of the raw materials is complete, add water to precipitate the product, and drain to obtain off-white solid 3-ethoxy-4-methoxybenzaldehyde oxime, dry 0.368mol, moisture 0.5%, purity 94.2%, yield 91.5%.

[0030] Put 0.9 mol (3.0 eq) of acetic anhydride and 0.3 mol of the 3-ethoxy-4-methoxybenzaldehyde oxime prepared above into the reaction flask, he...

Embodiment 3

[0033] Put 0.5mol of potassium carbonate, 0.5mol of isovanillin and 100ml of DMF into the reaction bottle, stir and heat to 100°C, slowly add 0.75mol (1.5eq) of bromoethane dropwise, and keep the reaction until the raw materials are reacted Extraction, concentration, and pumping to dryness gave 0.498 mol of white solid 3-ethoxy-4-methoxybenzaldehyde, 1.1% moisture, 98.7% purity, and 98.5% yield.

[0034] Drop into ethanol, hydroxylamine hydrochloride 0.48mol (1.2eq) in reaction flask, sodium hydroxide 0.48mol (1.2eq), the above-mentioned 3-ethoxyl-4-methoxybenzaldehyde 0.4mol that makes is heated up to 30- 40°C, heat-retaining reaction, until the reaction of the raw materials is complete, add water to precipitate the product, and drain to obtain off-white solid 3-ethoxy-4-methoxybenzaldehyde oxime, dry 0.38mol, moisture 0.52%, purity 94.8%, yield 94.5%.

[0035] Put 1.2mol (4.0eq) of acetic anhydride and 0.3mol of the 3-ethoxy-4-methoxybenzaldehyde oxime prepared above into t...

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Abstract

The invention discloses a 3-ethoxy-4-methoxy benzonitrile preparing method and relates to the technical field of organic synthesis. Isovanillin, bromoethane and hydroxylamine hydrochloride serve as raw materials for reaction, acetic anhydride serves as a dehydrating agent, activated carbon serves as a decolorizing agent, and 3-ethoxy-4-methoxy benzonitrile is obtained through ethylation, aldehyde oximation, acetic anhydride dehydration and absolute ethyl alcohol decoloration treatment. The raw materials adopted by the 3-ethoxy-4-methoxy benzonitrile preparing method are easy to obtain, reaction conditions are moderate, post-treatment is simple and convenient, the acetic anhydride can be recycled and reused, the production cost is low, environmental pollution is low, and the product yield and purity are high.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 3-ethoxy-4-methoxybenzonitrile. Background technique: [0002] 3-Ethoxy-4-methoxybenzonitrile is a pharmaceutical intermediate, its main function is to synthesize Otezla (apremilast) medicine, its chemical name is (S)-2-[1-(3-ethoxy yl-4-methoxyphenyl)-2-methanesulfonylethyl]-4-acetylaminoisoindoline-1,3-dione. Otezla is an oral, selective phosphodiesterase 4 (PDE4) inhibitor, the first and only FDA-approved PDE4 inhibitor for the treatment of plaque psoriasis. The oral drug Otezla has been approved by the FDA for the treatment of adults with moderate to severe plaque psoriasis (Plaque Psoriasis) who are candidates for phototherapy and systemic therapy. Compared with the existing therapeutic drug Apremilast Tablets, it has the characteristics of clear curative effect and less side effects, and the original research company is applying to expan...

Claims

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Application Information

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IPC IPC(8): C07C255/54C07C253/00
Inventor 杨青赵士民徐剑霄王松松汪洪湖刘淼
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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