Hofmann rearrangement, a classic organic reaction that transforms primary carboxamides into primary amines with one fewer carbon atom via an isocyanate intermediate. This guide covers:
Mechanism: Step-by-step breakdown (base-induced bromination, alkyl migration, and hydrolysis).
Key Examples:
Synthesis of anthranilic acid (precursor to saccharin and diuretics).
Conversion of nicotinamide to 3-aminopyridine (used in NSAIDs like piroxicam).
Production of 4-aminopyridine (potassium channel blocker for multiple sclerosis).
Pharmaceutical intermediates (phentermine, methylamine).
Applications:
Drug synthesis (analgesics, local anesthetics, sympathomimetics).
Carbon chain reduction in complex molecules.
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