One‐Pot Transformation of Aliphatic Carboxylic Acids into N ‐Alkylsuccinimides with NIS and NCS/NaI

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.