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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

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Abstract

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 °C in short reaction times via a simple experimental procedure.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran

    H. Valizadeh, M. Amiri, A. Shomali & F. Hosseinzadeh

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  1. H. Valizadeh
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  2. M. Amiri
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  3. A. Shomali
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  4. F. Hosseinzadeh
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Correspondence to H. Valizadeh.

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Valizadeh, H., Amiri, M., Shomali, A. et al. 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. JICS 8, 495–501 (2011). https://doi.org/10.1007/BF03249083

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  • DOI: https://doi.org/10.1007/BF03249083

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