Synthesis of melatonin (N-acetyl-5-methoxytryptamine) was written by Duan, Chuanfeng;Yang, Yijun. And the article was included in Yaoxue Xuebao in 1996.SDS of cas: 5367-32-8 This article mentions the following:
Melatonin was prepared in many steps from m-cresol via nitration, O-methylation, C-carboxycarbonylation, cyclization, decarboxylation, Mannich reaction with HNMe2-HCHO, cyanation, hydride reduction, and N-acetylation. The structure of all the compounds synthesized were characterized by elementary anal. and IR, MS and 1HNMR spectra. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8SDS of cas: 5367-32-8).
3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.SDS of cas: 5367-32-8
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem