Synthetic pathway of [2,4-dichloro-6-(3,5-dichloro-2-hydroxybenzamido)phenoxy]acetic acid

V. G. Dudarev; Дударев Владимир Геннадьевич; M. I. Vasendin; Васендин М. И.; A. V. Moskvin; Москвин Андрей Вадимович

doi:10.31857/S0514749224070074

Synthetic pathway of [2,4-dichloro-6-(3,5-dichloro-2-hydroxybenzamido)phenoxy]acetic acid

Authors: Dudarev V.G.¹, Vasendin M.I.¹, Moskvin A.V.¹
Affiliations:
1. St. Petersburg State Chemical and Pharmaceutical University
Issue: Vol 60, No 7 (2024)
Pages: 875-882
Section: Articles
URL: https://aspvestnik.ru/0514-7492/article/view/676689
DOI: https://doi.org/10.31857/S0514749224070074
EDN: https://elibrary.ru/RBIIRG
ID: 676689

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Abstract

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

Keywords

salicylanilides, reduction of nitro group, alkylation of nitrophenols, interphase catalysis, acylation, protecting groups

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