A Simple and Effective Procedure for the N-Permethylation of Amino-Substituted Naphthalenes

✍ Scribed by Vladimir I. Sorokin; Valery A. Ozeryanskii; Alexander F. Pozharskii

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 89 KB
• Volume: 2003
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200390085

✦ Synopsis

Abstract

A wide range of amino‐substituted naphthalenes can be N‐permethylated by the system Me~2~SO~4~/Na~2~CO~3~/H~2~O(alcohols) with good to excellent yields. Steric hindrance does not prevent the reaction. Some amines with electron‐withdrawing groups, especially at nonconjugated positions, are also alkylated. The procedure allows the combination of a reduction (catalytic or by tin dichloride in acidic media) and a methylation in a one‐pot process. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)