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Synthesis of 2-chlorine apellagrin

A synthetic method, the technology of clonicotinic acid, which is applied in the field of synthesis of pharmaceutical and pesticide intermediates, can solve the problems of unavailable and high prices, and achieve the effects of high synthesis yield, reduced reaction time, and good stability

Inactive Publication Date: 2009-02-18
NANKAI UNIV
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  • Application Information

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Problems solved by technology

In addition, the catalyst piperidine is used in the route, which is expensive and difficult to obtain.

Method used

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  • Synthesis of 2-chlorine apellagrin
  • Synthesis of 2-chlorine apellagrin
  • Synthesis of 2-chlorine apellagrin

Examples

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Embodiment Construction

[0039] Synthesis of Compound A (Vilsmerier Reaction)

[0040] 36.5g of N,N-dimethylformamide and 50ml of 1,2-dichloroethane were cooled in an ice bath to 0°C, and 300ml of dichloroethane containing 50g of solid phosgene was added dropwise with stirring (about 90min). Then it was stirred at room temperature for 1 hour to obtain solid compound A (Vilsmerier reagent).

[0041] Synthesis of Compound B

[0042] Under cooling in a water bath, 50.0 g of vinyl n-butyl ether and 50 ml of 1,2 dichloroethane mixed solution was added dropwise to compound A above, then stirred at room temperature for 1 hour, and reacted at 65° C. for 15 minutes. The 1,2-dichloroethane was removed under reduced pressure to obtain compound B.

[0043] Preparation of Compound C (Vinamidinium Salts)

[0044] Aqueous dimethylamine solution was added dropwise to Compound B, reacted at 70°C for 1 hour, added toluene and refluxed to dehydrate until anhydrous, and cooled to obtain solid Compound C, about 126g. ...

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Abstract

The present invention relates to a chemical synthesis method of an important intermediate 2-chlorine nicotine acid in medicine and pesticides, and a production process thereof. The route of synthesis reaction comprises: solid carbonyl chloride reacts with N, N-dimethyl formamide, then reacts with ethenyl n-butyl ether, added into dimethylamine aqueous solution, and reacts with cyano ethyl acetate after being dehydrated, the HCl gas is added, and the prepared compound is dissolved in alkaline solution. The raw materials, namely, the solid carbonyl chloride, the N, N-dimethyl formamide, the dimethylamine and the cyano ethyl acetate can be easily acquired. Only one step of distillation and purification is needed from the raw materials to the product; no harsh conditions are required in all the steps, the operation is simple and conducive to the environmental protection, and the present invention has remarkable social benefits and economic benefits, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the synthesis of medicine and pesticide intermediates, in particular to a synthesis method of 2-chloronicotinic acid. Background technique [0002] As we all know, with the development of pesticides and medicines in recent years, niacin series compounds have received more and more attention and applications. Among them, 2-chloronicotinic acid is used as a pesticide and a medical intermediate to prepare the new high-efficiency herbicide Nicosulfuron (Nicosufuron), the non-steroidal anti-inflammatory drug, the high-efficiency anti-inflammatory and analgesic drug Nifunicacid (Nifunicacid), and Prarol Fen (Pranoprofen) and HIV reverse enzyme inhibitor (Nevirapine), these products are in short supply at home and abroad. Therefore, the research on the preparation and production process of 2-chloronicotinic acid is of great significance. [0003] [0004] Niflumic Acid Nevirapine Nicosulfuron Diflufenamide [0005] There are man...

Claims

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Application Information

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IPC IPC(8): C07D213/803C07D213/80
Inventor 徐效华吕培谢龙观孙立冬
Owner NANKAI UNIV
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