Abstract
Participation of ‘activated DMSO’ in the one-pot
transformation of aldehydes to nitriles has been described by reacting
aldehydes with NH2 OH˙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
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General Procedure
for Nitrile Synthesis from Aldehydes
2 OH˙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 H2 O.
The solid precipitated was collected by filtration, washed with
H2 O, and dried under suction to afford the corresponding
nitrile in excellent yield. Alternatively, the reaction mixture
could be poured onto H2 O and extracted with Et2 O.
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.
