Pyrazoles by dealkylation of pyrazolium salts

Abstract

Abstract A rapid, convenient conversion of 1,2‐dimethylpyrazolium salts ( 1 ) to 1‐methylpyrazoles ( 2 ) is accomplished in piperidine or 3‐methylpiperidine at temperatures ≥ 106°. This demethylation represents a particularly useful procedure for the synthesis of 3‐ and 5‐substituted aminopyrazoles, which are not readily obtainable by other methods. The 50:50 mixture of piperidinopyrazole isomers 2b can be obtained directly by treating 3‐chloro‐1,2‐dimethyl‐5‐phenylpyrazolium iodide (3b ) with piperidine in ethanol at 106°.