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Preparation method for 4-aminoacetophenone

An aminoacetophenone, hydroxyl technology, applied in a new preparation field of p-aminoacetophenone, can solve the problems of harsh reaction conditions, many by-products, strong reagent corrosion and the like

Inactive Publication Date: 2013-02-13
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the main defect of above-mentioned two kinds of preparation methods is that the reaction conditions are harsh, the reagents used are highly corrosive, there are many by-products, the purification and separation of products is complicated, and the yield is low.

Method used

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  • Preparation method for 4-aminoacetophenone
  • Preparation method for 4-aminoacetophenone
  • Preparation method for 4-aminoacetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the preparation of N-(4-acetylphenyl)-2-hydroxyl-2-methylpropionamide

[0019] Dissolve 3.00g (22.06mmol) of p-hydroxyacetophenone in 15mL of DMA in a 100mL round bottom flask, add 2.65g (66.18mmol) of sodium hydroxide and stir the reaction at 15-25°C for 1 hour. Subsequently, 11.00 g (66.18 mmol) of 2-bromo-2-methylpropanamide was added and the reaction was stirred at 15-25°C for 5 hours (the product of this step was directly carried to the next step without isolation). After the reaction, 7.94g (198.54mmol) sodium hydroxide was added and stirred at 45-50°C for 1 hour, and finally 30mL of water was added and stirred at room temperature for crystallization. After suction filtration and natural air drying, 2.90 g of yellow crystal powder was obtained with a yield of 59.5%, which can be directly used in the next reaction without further purification.

[0020] Similarly, substitute 2-chloro-2-methylpropanamide for 2-bromo-2-methylpropanamide, potassium hydro...

Embodiment 2

[0027] Embodiment 2: the preparation of p-aminoacetophenone

[0028] Dissolve 4.72 g (118.08 mmol) of sodium hydroxide in 13 mL of water in a 100 mL round bottom flask, then add 13 mL of DMA and 2.90 g (13.12 mmol) of N-(4-acetylphenyl)-2-hydroxy- 2-methylpropanamide, and heated to reflux at 90°C for 1 hour. After the reaction was completed, 26 mL of water was added and stirred at room temperature for crystallization. After suction filtration and natural air drying, 1.55 g of yellow crystal powder was obtained with a yield of 87.6% and a total yield of 52.1%.

[0029] Similarly, replace sodium hydroxide with potassium hydroxide or calcium hydroxide, and replace N,N-dimethylacetamide (DMA) with N,N-dimethylformamide (DMF) or dimethylsulfoxide (DMSO). ), change the hydrolysis reaction temperature and reaction time to obtain p-aminoacetophenone, and the results are listed in Table 2.

[0030]

[0031] Table 2. Preparation of p-aminoacetophenone

[0032]

[0033]

[003...

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Abstract

The invention belongs to the medical technical field, and relates to a bran-new synthetic route for preparing 4-aminoacetophenone. Through a Williamson ether synthesis method and Smiles rearrangement reaction, benzamide compounds are produced, then the 4-aminoacetophenone preparation is finished after hydrolysis. Reaction condition is gentle, and flammable and combustible reagents and high-toxic reagents are not involved. Yield coefficient is higher than that of the preparation method in documents. The preparation method is an economical and practical synthetic method, and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a new preparation method of p-aminoacetophenone. Background technique [0002] 4-Aminoacetophenone is an extremely important pharmaceutical intermediate and raw material, for example, it can be used to synthesize cretin and flurbiprofen. Ketansu is widely used in the treatment of diseases such as bronchial asthma, chronic asthmatic bronchitis and emphysema, and it is also a new type of animal feed additive developed abroad in recent years. Flurbiprofen is a non-steroidal anti-inflammatory analgesic, developed by the British Boots Company in 1976, and has been included in the 1988 edition of the British Pharmacopoeia. At present, flurbiprofen has been sold in more than 70 countries. It is clinically applicable to rheumatoid arthritis, osteoarthritis and flexural spondylitis. Advantages such as small side effects. [0003] The preparation method of existing p-aminoacetophenone main...

Claims

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Application Information

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IPC IPC(8): C07C225/22C07C221/00
Inventor 胡春孙冰刘晓平黄二芳金辄
Owner SHENYANG PHARMA UNIVERSITY
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