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One‐Pot Transformation of Aliphatic Carboxylic Acids into N ‐Alkylsuccinimides with NIS and NCS/NaI
Author(s) -
Nakai Yuhta,
Moriyama Katsuhiko,
Togo Hideo
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501315
Subject(s) - chemistry , primary (astronomy) , yield (engineering) , hydrazine (antidepressant) , carboxylic acid , organic chemistry , medicinal chemistry , alkyl , reaction conditions , catalysis , physics , materials science , chromatography , astronomy , metallurgy
Primary aliphatic carboxylic acids were treated with N ‐iodosuccinimide (NIS) in 1,2‐dichloroethane to form the corresponding alkyl iodides under warming conditions. Based on these results, those aliphatic carboxylic acids were treated with NIS, followed by the reaction with K 2 CO 3 to give the corresponding N ‐alkylsuccinimides in good yields in one pot. Moreover, those aliphatic carboxylic acids were treated with N ‐chlorosuccinimide (NCS) and NaI, followed by the reaction with K 2 CO 3 to provide the corresponding N ‐alkylsuccinimides in good to moderate yields in one pot. By using the present method, successive treatment of primary aliphatic carboxylic acids (10 mmol) with NIS, K 2 CO 3 , and then hydrazine provided the corresponding decarboxylated primary amines in good yield.