Ionic Liquid 1-(3-Trimethoxysilylpropyl)-3-methylimidazolium Nitrite as a New Reagent for the Efficient Diazotization of Aniline Derivatives and In Situ Synthesis of Azo Dyes

A new ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of arylamines into their corresponding diazonium salts which were converted into their related azo dyes via the in situ azo-coupling with aniline derivatives or phenolic compounds. The diazotization of anilines in this ionic liquid and subsequent azo-coupling generated the related azo dyes in good to excellent yields at 0-5 degrees C in short reaction times via a simple experimental procedure.