138113-07-2

Basic information

• Product Name: 2-(7-Methoxynaphthalen-1-yl)acetamide
• Synonyms: 2-(7-Methoxynaphthalen-1-yl)acetamide;(7-Methoxy-1-naphthyl)acetamide;7-Methoxy-1-naphthaleneacetamide;(7-Methoxy-[1]naphthyl)-acetic acid aMide;AgoMelatine IMp.VIII;AgoMelatine IMpurity H;Agomelatine Impurity 6;2-(7-Methoxyphthalen-1-yl)acetamide
• CAS NO: 138113-07-2
• Molecular Formula: C₁₃H₁₃NO₂
• Molecular Weight: 215
• EINECS: -0
• Mol File: 138113-07-2.mol

Chemical Properties

• Boiling Point: 452.7±28.0 °C at 760 mmHg
• Flash Point: 249.1±20.3 °C
• Appearance: /
• Density: 1.188
• Vapor Pressure: 0.0±1.1 mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Water (Slightly)
• CAS DataBase Reference: 2-(7-Methoxynaphthalen-1-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(7-Methoxynaphthalen-1-yl)acetamide(138113-07-2)
• EPA Substance Registry System: 2-(7-Methoxynaphthalen-1-yl)acetamide(138113-07-2)

Safety Data

• Hazardous Substances Data: 138113-07-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(7-Methoxynaphthalen-1-yl)acetamide is used as a key intermediate in the synthesis of various melatonin analogs, such as Agomelatine Impurity 6. These analogs contain a naphthalene moiety instead of the traditional indole nucleus and exhibit high affinity for the melatonin receptor. The compound plays a crucial role in the development of novel therapeutic agents targeting melatonin receptors, which can be beneficial for treating various sleep disorders, mood disorders, and other conditions related to the circadian rhythm.
Used in Chemical Synthesis:
In the chemical industry, 2-(7-Methoxynaphthalen-1-yl)acetamide can be utilized as a building block for the synthesis of a wide range of naphthalene-based compounds with diverse applications. These applications may include the development of new materials, dyes, pigments, and other specialty chemicals that can be used in various industrial processes. The compound's unique structural features make it a valuable starting material for the creation of novel chemical entities with potential commercial and technological significance.

InChI:InChI=1S/C13H13NO2/c1-16-11-6-5-9-3-2-4-10(7-13(14)15)12(9)8-11/h2-6,8H,7H2,1H3,(H2,14,15)

Upstream product

• 5060-82-2 7-methoxy-2-naphthol 
• 27533-69-3 2-(1,2-dihydro-6-methoxynaphthalen-4-yl)acetic acid 
• 6836-22-2 2-(7-methoxynaphthalen-1-yl)acetic acid 
• 6836-23-3 (7-methoxy-1-naphthyl)acetic acid chloride 
• 6836-20-0 ethyl (7-methoxy-1,2,3,4-tetrahydro-1-naphthalenylidene)acetate 
• 63319-95-9 [7-Methoxy-3,4-dihydro-2H-naphthalen-(1E)-ylidene]-acetic acid 
• 27532-26-9 ethyl (1,2,3,4-tetrahydro-7-methoxy-1-naphthyl)acetate 
• 6836-19-7 7-Methoxy-1-tetralone 
• 27533-70-6 2-(7-methoxy-3,4-dihydro-naphthalen-1-yl)-acetic acid ethyl ester 
• 6836-21-1 ethyl 2-(7-methoxynaphthalen-1-yl)acetate 

Downstream Products

• 138113-09-4 2-(7-methoxynaphth-1-yl)ethylamine 
• 138112-76-2 agomelatine 
• 138112-95-5 S 20255 
• 138112-91-1 S 20254 
• 138113-02-7 S 20305 
• 138112-77-3 S 20099 
• 138113-13-0 N-[2-(7-methoxy-1-naphthyl)ethyl]cyclobutanecarboxamide 
• 138112-87-5 S 20253 
• 138112-80-8 S 20303 
• 138113-03-8 N-[2-(7-methoxy-1-naphthyl)ethyl]cyclopropanecarboxamide 
• 138112-99-9 N-[2-(7-Methoxynaphth-1-yl)Ethyl]-Butyramide 
• 138112-78-4 S 20100 
• 138112-79-5 N-[2-(7-methoxy-1-naphthyl)ethyl]propionamide 
• 138113-08-3 (7-methoxy-1-naphthyl)acetonitrile 

Relevant articles and documents

The preparation method of the agomelatine intermediate

The invention relates to a preparation method of an agomelatine intermediate. The method specifically comprises the following steps: by using 7-methoxyl tetrahydronaphthalene-1-one and diethyoxyl phosphoryl ethyl acetate as initial raw materials, carrying out condensation, dehydrogenation, ammonolysis and dehydration to obtain the agomelatine intermediate, namely a compound shown in a formula (IV). The preparation method provided by the invention is economical in preparation process and suitable for massively preparing the agomelatine intermediate with high yield.

PROCESS FOR THE SYNTHESIS OF AGOMELATINE

Process for the industrial synthesis of the compound of formula (I):

A simple and efficient procedure for synthesis of agomelatine

A simple and efficient process for the large scale preparation of agomelatine, an antidepressant drug is described. Agomelatine was synthesized from 7-methoxy-1-tetralone in five steps. The route reported employs readily, commercially viable starting materials, reagents and potentially be utilized for the process of synthesis of agomelatine.

PROCESS FOR PREPARATION OF AGOMELATINE AND CRYSTALLINE FORM I THEREOF

An improved process for the preparation of agomelatine of formula (I) and a new process for the preparation of crystalline form I of agomelatine are provided.

PROCESS FOR THE PREPARATION OF AGOMELATINE

The present invention relates to a process for the manufacture of N-[2-(7-methoxy-1-naphthalenyl) ethyl]acetamide (Agomelatine) with improved yield and reduced level of N- acetyl-N-[2-(7-methoxy-1-naphthalenyl) ethyl]acetamide impurity.

AGOMELATINE AND PHARMACEUTICAL COMPOSITIONS THEREOF

Agomelatine crystal, which is a drug for treating depression, and pharmaceutical compositions thereof are provided. The X-ray powder diffraction spectra of such agomelatine crystal, which is irradiated by Cu-Kα and showed by 20(degree), has characteristic diffraction peaks at 12.84, 13.84, 16.14, 18.56, 19.12, 20.86, 21.20, 23.84; its IR absorption pattern has characteristic absorption peaks at about 3234, 3060, 2940, 1638, 1511, 1436, 1249, 1215, 1184, 1032, 908, 828, 755, 588 cm-1; and its DSC endothermic transition temperature is 97.6°C. The use of the agomelatine crystal as an active ingredient in preparing a medicament for the treatment of depression is also provided.

SUBSTITUTED NAPHTHALENES

Disclosed herein are substituted naphthalene-based melatonin (MT) receptor modulators and/or 5-HT receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.