Hammick reaction

The Hammick reaction is a chemical reaction describes as a thermal decarboxylation of α-picolinic (or related) acids in the presence of carbonyl compounds to form 2-pyridyl-carbinols.



Using p-cymene as solvent has been shown to increase yields.

Reaction mechanism
Upon heating α-picolinic acid will spontaneously decarboxylate forming a zwitterion (2). 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.