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DOI: 10.1055/s-0030-1261181
A Practical and Cost-Efficient, One-Pot Conversion of Aldehydes into Nitriles Mediated by ‘Activated DMSO’
Publication History
Publication Date:
12 August 2011 (online)

Abstract
Participation of ‘activated DMSO’ in the one-pot transformation of aldehydes to nitriles has been described by reacting aldehydes with NH2OH˙HCl in DMSO in the absence of any added base or catalyst. The method is applicable to access a wide range of aromatic, heterocyclic, and aliphatic nitriles, in which only water is a byproduct. A straightforward and practical procedure is demonstrated on a multigram scale.
Key words
activated DMSO - nitriles - aldehydes - dehydration - catalyst
- Supporting Information for this article is available online:
- Supporting Information (PDF)
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References and Notes
The products were not contaminated with any side products, such as Pummerer rearrangement products.
18
General Procedure
for Nitrile Synthesis from Aldehydes
A mixture of
aldehyde (1 equiv) and NH2OH˙HCl (1.1 equiv)
in DMSO (3-5 volumes depending on homogeneity of mixture)
was stirred at 90 ˚C for 1-2 h. When
the reaction was completed as confirmed by TLC (5% EtOAc
in hexane), the mixture was cooled and diluted with H2O.
The solid precipitated was collected by filtration, washed with
H2O, and dried under suction to afford the corresponding
nitrile in excellent yield. Alternatively, the reaction mixture
could be poured onto H2O and extracted with Et2O.
The organic phase could be evaporated to afford the nitrile with
good purity and yield. This method is suitable for the isolation
of liquid and aliphatic nitriles.