University Chemistry ›› 2015, Vol. 30 ›› Issue (3): 43-46.doi: 10.3866/pku.DXHX2010343

• Chemistry Laboratory • Previous Articles     Next Articles

The Synthesis of Melatonin——An Exploratory Organic Chemistry Experiment

Guan Ling, Xu Xuanfeng, Bian Lei, Gao Yang, Zhang Qihan   

  1. Experimental Chemistry Center, Peking University, Beijing 100871, China
  • Published:2015-06-25

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

MSC2000: 

  • O6