Reaction of Bromomethylisoquinolines with Alcohols and Amines

Abstract

The reactions of 8-bromomethyl-l-methylisoquinoline hydrobromide 1 with sodium hydroxide and sodium alkoxide (alkoxide = methoxide, ethoxide, propoxide, and isopropoxide) gave the corresponding 8-hydroxymethyl and 8-alkoxymethyl 1-methylisoquinolines (3 a and 3 b∼e), respectively. The reaction of 1, 8-bis(bromomethy)isoquinoline hydrobromide 2 with sodium alkoxides gave 1, 8-bis(alkoxymethyl)isoquinolines 4 a∼d. The reactions of the compound 1 with ammonia and alkylamines (alkyl =methyl, ethyl, propyl, and isopropyl) gave 8-aminomethyl and 8-alkylaminomethyl-l-methylisoquinolines (5 a and 5 b∼e). On the reaction of the compound 2 with the same amines, the ring closure occurred to give 1 H-2, 3~dihydrobenzo[de][l, 7]naphthyridine derivatives 6 a∼e. © 1991, The Chemical Society of Japan. All rights reserved.