The Hammick reaction
, named after Dalziel Hammick
, is a chemical reaction
described as a thermal decarboxylation
(or related) acids
in the presence of carbonyl
compounds to form 2-pyridyl
Using p-cymene as solvent has been shown to increase yields.
Upon heating α-picolinic acid will spontaneously decarboxylate forming a zwitterion
). In the presence of a strong electrophile
, such as an aldehyde
, the zwitterion will react with the carbonyl faster than protonating. Upon proton transfer the desired carbinol (4
) is formed.