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

被引：0
|
作者：
Dudarev, V. G. [1 ]
Vasendin, M. I. [1 ]
Moskvin, A. V. [1 ]
机构：
[1] St Petersburg State Chem & Pharmaceut Univ, St Petersburg 197022, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 60卷 / 07期
关键词：
salicylanilides; reduction of nitro group; alkylation of nitrophenols; interphase catalysis; acylation; protecting groups; SALICYLANILIDES; DERIVATIVES; INHIBITORS;
D O I：
10.1134/S1070428024070029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
ynthetic 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.
引用
收藏
页码：1157 / 1163
页数：7
相关论文
共 50 条
  • [31] 3,5-Dichloro-6-methylpyridin-2-amine
    Fun, Hoong-Kun
    Kia, Reza
    Maity, Annada C.
    Maity, Sibaprasad
    Goswami, Shyamaprosad
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O97 - U2112
  • [32] Bis[2,4-dichloro-6-(ethyliminomethyl)phenolato-κ2N,O]nickel(II)
    Huang, Qiu Ping
    Zhang, Shu Hua
    Guo, Jing Jing
    Feng, Chao
    Tang, Fu Shun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : M1611 - +
  • [33] FUNGITOXICITY OF 2,4-DICHLORO-3,5-DINITROBENZOATES
    SUMMERS, LA
    TURNER, JAW
    NATURE, 1963, 197 (486) : 495 - &
  • [34] 2,4-Dichloro-N-(3,5-dichlorophenyl)benzenesulfonamide
    Rodrigues, Vinola Z.
    Foro, Sabine
    Gowda, B. Thimme
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2976 - U849
  • [35] 2,4-Dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide
    Rodrigues, Vinola Z.
    Foro, Sabine
    Gowda, B. Thimme
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2842 - +
  • [36] trans-Bis{2,4-dichloro-6-[(3-cyclohexylaminopropylimino)methyl] phenolato}cobalt(III) perchlorate
    Yuan, CL
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : M2112 - M2114
  • [37] 2,4-Dichloro-6-methoxyquinoline
    Subashini, R.
    Hathwar, Venkatesha R.
    Manivel, P.
    Prabakaran, K.
    Khan, F. Nawaz
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O370 - U2584
  • [38] catena-poly[[[2,4-dichloro-6-(pyridin-2-ylmethyliminomethyl)phenolato]copper(II)]-μ-thiocyanato]
    You, ZL
    Zhu, HL
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : M421 - M423
  • [39] CARBOXYLATION OF 2,4-DICHLOROPHENOL TO POTASSIUM 3,5-DICHLORO-2-HYDROXYBENZOATE
    SHAKIROV, LG
    BIKKULOV, AZ
    SMOLYANETS, EF
    JOURNAL OF APPLIED CHEMISTRY OF THE USSR, 1981, 54 (05): : 925 - 928
  • [40] Di-μ-thiocyanato-bis({2,4-dichloro-6-[2(diethylamino) ethyliminomethyl]-phenolat}copper(II))
    Li, Xian-Wen
    Qiu, Yang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : M218 - U2099
12345