The Hoffmann Bromamide Degradation is used to prepare primary amines from amides.

• Reaction: $R-CON{H}_2+B{r}_2+4NaOH\to R-N{H}_2+N{a}_{2}C{O}_3+2NaBr+2H_{2}O$
• The reaction involves the migration of an alkyl/aryl group from the carbonyl carbon to the nitrogen atom.
• The carbonyl carbon is lost as carbonate ion, resulting in an amine that has one less carbon atom than the starting amide.
• Intermediate: An alkyl isocyanate ($R-N=C=O$) is formed during the mechanism.