Melamine Nitrate: A Novel and Efficient Reagent for Regioselective Nitration of Phenols

Yong-Qiang Chen,Hong Jiang

doi:10.1155/2011/753142

Abstract

Melamine nitrate (MN) as a novel nitration reagent was easily prepared. Regioselective nitration of phenols to their corresponding o-nitrophenols occurred using MN with p-toluenesulfonic acid as catalyst in good to excellent yields. A distinct advantage of this method is the easy separation of products by simple filtration.

Highlights

Nitration of aromatic compounds is one of the most important and widely studied reactions and industrial processes
Different other catalytic acids like, acetic acid, benzoic acid, and sulfuric acid were tested but they either gave trace product or very complicated products; so ptoluenesulfonic acid was chosen as catalytic acid
Though phenolic compounds bearing electron donating groups well behaved to afford the o-nitrophenolic compounds selectively, those with even moderately deactivating groups, such as 2-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, methyl 2-hydroxybenzoate, and 4-hydroxybenzoic acid have no reaction at room temperature or under reflux by Thin-layer chromatography (TLC) monitor

Summary

Introduction

Nitration of aromatic compounds is one of the most important and widely studied reactions and industrial processes. In this paper we prepared the melamine nitric acid complex (MN) (Figure 1) and used it as nitration reagent. We report this efficient and facile nitration procedure for phenols using MN (Scheme 1).

Results

Conclusion