99417-10-4

Upstream product

• 99416-97-4 ethyl 1-hydroxy-7-methoxy-1,2,3,4-tetrahydro-1-naphthaleneacetate 
• 6836-21-1 ethyl 2-(7-methoxynaphthalen-1-yl)acetate 
• 4521-28-2 4-(4-Methoxyphenyl)butyric acid 
• 6836-19-7 7-Methoxy-1-tetralone 
• 99416-99-6 2-(7-methoxynaphthalen-1-yl)ethan-1-ol 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 99439-47-1 3-<2-(7-methoxy-1-naphthyl)ethyl>-2-cyclohexeneone 
• 139525-77-2 2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride 
• 138112-76-2 agomelatine 

Relevant academic research and scientific papers

PROCESS FOR THE MANUFACTURE OF AGOMELATINE AND ITS INTERMEDIATE

A process for the manufacture of agomelatine and its intermediate N-[2-(7-methoxy-1-naphthyl)ethyl] phthalimide comprises: reacting 7-methoxy-1-naphthyl ethanol (III) with benzenesulfonyl chloride to obtain 7-methoxy-1-naphthylethyl benzene sulfonate (IV), which is reacted with potassium phthalimide to produce N-[2-(7-methoxy-1-naphthyl)ethyl] phthalimide (II); and subjecting N-[2-(7-methoxy-1-naphthyl)ethyl] phthalimide (II) to alkaline hydrolysis and acetylation, to obtain agomelatine.

Methoxybenzopyrene 4,5-Oxides Labeled with Carbon-13: Electronic Effects in the NIH Shift

The synthesis of 9-methoxy-4,5-dihydrobenzopyrene-4-13C4,5-oxide and -5-13C4,5-oxide and of 8-methoxy-4,5-dihydrobenzopyrene-4-13C4,5-oxide is reported.The compounds were synthesized in yields of 15percent each from unlabeled precursors. 13C NMR analysis of the conversion of the 4,5-oxides to 4-phenols and 5-phenols (NIH shift) revealed a very strong electronic effect of a 9-methoxy substituent, which gave only the 4-phenol, and a significant but weaker effect of an 8-methoxy substituent, which gave both phenols with the 5-phenol predominating.