Isatoic Anhydride

Chemical properties

BEIGE TO BROWN POWDER

The Uses of Isatoic Anhydride

Isatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors.

What are the applications of Application

Isatoic Anhydride is a potent inactivator of chymotrypsin

Definition

A bicyclic molecule composed of a benzene ring attached at the oand mpositions to a heterocyclic ring. It forms useful anthranilic acid derivatives by reaction with hydrogen.

Preparation

Phosphorus tribromide (0.035 mol) was added to a solution of N-carbethoxy- or N-carbobenzoxy-anthranilic acid (0.1 mol;prepared by coupling anthranilic acid with the corresponding carbalkoxy chloride in the usual way) in anhydrous diethyl ether (100 mL). After 24 h at room temperature, isatoic anhydride had separated as a microcrystalline product. It was collected by filtration, washed with dry diethyl ether, and recrystallized from ethanol. Yield ca. 90%.

Flammability and Explosibility

Non flammable

Purification Methods

Recrystallise it from EtOH or 95% EtOH (30mL/g) or dioxane (10mL/g) and dry it in a vacuum. [Wagner & Fegley Org Synth Coll Vol III 488 1955, Ben-Ishai & Katchalski J Am Chem Soc 74 3688 1952, UV: Zentmyer & Wagner J Org Chem 14 967 1949, Beilstein 27 II 299, 27III/IV 3330.]