15371-06-9

Basic information

• Product Name: 3-acetamidophthalic acid
• Synonyms: 3-acetamidophthalic acid;3-(Acetylamino)phthalic acid;1,2-Benzenedicarboxylic acid, 3-(acetylamino)-;3-Acetamido-1,2-benzenedicarboxylic acid;Einecs 239-404-9;Apremilast Impurity B
• CAS NO: 15371-06-9
• Molecular Formula: C₁₀H₉NO₅
• Molecular Weight: 223.18216
• EINECS: 239-404-9
• Mol File: 15371-06-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 260 °C
• Boiling Point: 518.2°Cat760mmHg
• Flash Point: 267.2°C
• Appearance: /
• Density: 1.512g/cm³
• Vapor Pressure: 1.45E-11mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.54±0.10(Predicted)
• CAS DataBase Reference: 3-acetamidophthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-acetamidophthalic acid(15371-06-9)
• EPA Substance Registry System: 3-acetamidophthalic acid(15371-06-9)

Safety Data

• Hazardous Substances Data: 15371-06-9(Hazardous Substances Data)

Usage

Uses

3-Acetamidophthalic Acid is an impurity of Apremilast (A729700); an oral phosphodiesterase 4 inhibitor used in the treatment of psoriatic arthritis. Apremilast EP Impurity B

InChI:InChI=1/C10H9NO5/c1-5(12)11-7-4-2-3-6(9(13)14)8(7)10(15)16/h2-4H,1H3,(H,11,12)(H,13,14)(H,15,16)

Upstream product

• 5434-20-8 3-aminophthalic acid 
• 75-36-5 acetyl chloride 
• 603-11-2 3-nitrophthalic acid 
• 108-24-7 acetic anhydride 
• 6118-65-6 3-acetamidophthalimide 

Downstream Products

• 608141-41-9 Apremilast 

Relevant articles and documents

ANTI-INFLAMMATORY COMPOUNDS AND METHODS FOR THEIR MANUFACTURE

The present invention relates to an improved process for the preparation of anti-inflammatory compounds, such as N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3- dioxoisoindol-4-yl]acetamide or a salt or solvate thereof and novel polymorphic forms thereof.

An improved economical process for preparation of apremilast and identified their impurities

The object of the present study is to provide an improved and commercially viable process for the preparation of apremilast, which is simple, cost effective and non-hazardous. In this process avoided the usage of acetic anhydride and high temperature. In this method, an alternative process using protected 3-aminophthalic acid (2) with acetyl chloride in the presence of triethanolamine as catalyst in dichloromethane solvent at 0 to 5 °C for 1 h. then followed by condensed with compound 3 to get the final compound 4. Besides, there were two unknown impurities like 3-(amino-1,3-dioxoisoindolin-2-yl)phthalic acid (5) and 4-aminoisobenzofuran-1,3-dione (6) identified by HPLC. A thorough study has been under taken to synthesize and characterize these unknown impurities. This improved process has a number of industrial advantages, such as economical material cost and relatively high yield. The structure of the synthesized compounds was elucidated by IR, 1H NMR, 13C NMR, mass spectroscopy and elemental analyses.