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...

Full description

Saved in:
Bibliographic Details
Published in:Russian journal of organic chemistry 2024-07, Vol.60 (7), p.1157-1163
Main Authors: Dudarev, V. G., Vasendin, M. I., Moskvin, A. V.
Format: Article
Language:English
Subjects:
Acetic acid
Aniline
Carboxyl group
Chemistry
Chemistry and Materials Science
Chlorides
Dimethyl acetamide
Organic Chemistry
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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-2 H -1,4-benzoxazin-3(4 H )-one.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428024070029