2,4-二氯-6-(3,5-二氯-2-羟基苯甲酰胺基)苯氧基]乙酸的合成途径

IF 0.8 4区化学 Q4 CHEMISTRY, ORGANIC

Russian Journal of Organic Chemistry Pub Date : 2024-10-14 DOI:10.1134/S1070428024070029

V. G. Dudarev, M. I. Vasendin, A. V. Moskvin

{"title":"2,4-二氯-6-(3,5-二氯-2-羟基苯甲酰胺基)苯氧基]乙酸的合成途径","authors":"V. G. Dudarev, M. I. Vasendin, A. V. Moskvin","doi":"10.1134/S1070428024070029","DOIUrl":null,"url":null,"abstract":"Synthetic route of 3,5-dichlorosalicylic acid anilide containing the carboxymethoxy group in the aniline fragment in ortho-position to amide group has been suggested. The obtained intermediate (2,4-dichloro-6-nitrophenoxy)-N,N-dimethylacetamide has been reduced into the amine and acylated with 3,5-dichloro-2-hydroxybenzoyl chloride, and then protective N,N-dimethylamide group has been selectively hydrolyzed in an alkaline medium. Without protection of the carboxyl group, the reaction with 3,5-dichloro-2-hydroxybenzoyl chloride has afforded mainly 6,8-dichloro-2H-1,4-benzoxazin-3(4H)-one.","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 7","pages":"1157 - 1163"},"PeriodicalIF":0.8000,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthetic Pathway of [2,4-Dichloro-6-(3,5-dichloro-2-hydroxybenzamido)phenoxy]acetic Acid\",\"authors\":\"V. G. Dudarev, M. I. Vasendin, A. V. Moskvin\",\"doi\":\"10.1134/S1070428024070029\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Synthetic route of 3,5-dichlorosalicylic acid anilide containing the carboxymethoxy group in the aniline fragment in ortho-position to amide group has been suggested. The obtained intermediate (2,4-dichloro-6-nitrophenoxy)-N,N-dimethylacetamide has been reduced into the amine and acylated with 3,5-dichloro-2-hydroxybenzoyl chloride, and then protective N,N-dimethylamide group has been selectively hydrolyzed in an alkaline medium. Without protection of the carboxyl group, the reaction with 3,5-dichloro-2-hydroxybenzoyl chloride has afforded mainly 6,8-dichloro-2H-1,4-benzoxazin-3(4H)-one.\",\"PeriodicalId\":766,\"journal\":{\"name\":\"Russian Journal of Organic Chemistry\",\"volume\":\"60 7\",\"pages\":\"1157 - 1163\"},\"PeriodicalIF\":0.8000,\"publicationDate\":\"2024-10-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1134/S1070428024070029\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070428024070029","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

3,5-Dichlorosalicylic acid anilide（3,5-二氯水杨酸苯胺）的合成路线被提出，该苯胺片段中的羧基甲氧基位于酰胺基团的正交位置。得到的中间体（2,4-二氯-6-硝基苯氧基）-N,N-二甲基乙酰胺被还原成胺，并与 3,5-二氯-2-羟基苯甲酰氯酰化，然后保护性的 N,N-二甲基酰胺基团在碱性介质中被选择性水解。在不保护羧基的情况下，与 3,5-二氯-2-羟基苯甲酰氯反应主要得到 6,8-二氯-2H-1,4-苯并恶嗪-3(4H)-酮。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthetic Pathway of [2,4-Dichloro-6-(3,5-dichloro-2-hydroxybenzamido)phenoxy]acetic Acid

查看原文本刊更多论文

Synthetic Pathway of [2,4-Dichloro-6-(3,5-dichloro-2-hydroxybenzamido)phenoxy]acetic Acid

Synthetic route of 3,5-dichlorosalicylic acid anilide containing the carboxymethoxy group in the aniline fragment in ortho-position to amide group has been suggested. The obtained intermediate (2,4-dichloro-6-nitrophenoxy)-N,N-dimethylacetamide has been reduced into the amine and acylated with 3,5-dichloro-2-hydroxybenzoyl chloride, and then protective N,N-dimethylamide group has been selectively hydrolyzed in an alkaline medium. Without protection of the carboxyl group, the reaction with 3,5-dichloro-2-hydroxybenzoyl chloride has afforded mainly 6,8-dichloro-2H-1,4-benzoxazin-3(4H)-one.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Russian Journal of Organic Chemistry 化学-有机化学

CiteScore

1.40

自引率

25.00%

发文量

139

审稿时长

3-6 weeks

期刊介绍： Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.