Abstract:

The synthesis of melatonin is an exploratory experiment completed by second-year undergraduates. The synthetic approach based on the procedure provided by the patent is a short, simple, and industrially feasible process suitable for organic chemistry laboratory. The formation of the indole ring is completed based on Japp-Klingemann reaction and Fischer indole synthesis using phthalimide, 1,3-dibromo-propane, ethyl acetoacetate and 4-anisidine as the main reactants. Melatonin forms after hydrolyzation, decarboxylation and acetylation of the indole ring. The optimization of conditions is also discussed briefly.

Key words: Exploratory experiment, Melatonin, Japp-Klingemann reation, Multi-step synthesis