RSC Advances
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DOI: 10.1039/C5RA14702F
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iodovanillin is an important intermediate for the synthesis of
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Fig. 1 Recovery and reusability of BMPDCI
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to recover 1-butyl-3-methylpyridinium chloride (BMPCI).
Addition of ICl (1.2 eq.) to 1-butyl-3-methylpyridinium chloride
in water and dichloromethane (as reported in Scheme 1),
afforded 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI),
which was used for further iodination reactions. The 1-butyl-3-
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reused for up to five runs with >93% yield of the iodinated
product and without any loss of activity (Fig.1). To exhibit the
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Conclusion
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1-butyl-3-methyl-pyridinium dichloroiodate which can be easily
prepared provides a recyclable iodinating agent for activated
aromatic amines in the absence of any solvent. Main advantages
are no need of any oxidant/catalyst/base, simple practical
procedure, good yields, recyclable iodinating reagent, renders
this protocol environmentally benign. The reagent is easliy
prepared from commercial materials viz. 3-methylpyridine,
which is the main precursor for the synthesis of nicotinic acid.
This work successfully realised the dual role of 1-butyl-3-
methyl-pyridinium dichloroiodate as an iodinating reagent and
solvent.
Acknowlegedments
29. O. Bortolini, M. Bottai, C. Chiappe, V. Conte and D.
A. D. wishes to thank CSIR-Networking Project CSC-0130 for
their generous financial support. The authors thank Dr. Sanjay
P. Borikar for providing the necessary GC and GCMS analysis.
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