Isatoic anhydride is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

derived from

anthranilic acid Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ''ortho''-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic f ...

. A white solid, it is prepared by reaction of anthranilic acid with

phosgene Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, espe ...

Reactions

Hydrolysis gives carbon dioxide and anthranilic acid. Alcoholysis proceeds similarly, affording the ester: :C₆H₄C₂O₃NH + ROH → C₆H₄(CO₂R)(NH₂) + CO₂ Amines also effect ring-opening. Active methylene compounds and carbanions replace oxygen giving hydroxy quinolinone derivatives. Deprotonation followed by alkylation gives the N-substituted derivatives. Sodium azide gives the benz

imidazolone Imidazolones are a family of heterocyclic compounds, the parents of which have the formula OC(NH)2(CH)2. Two isomers are possible, depending on the location of the carbonyl (CO) group. The NH groups are nonadjacent. A common route to imidazol-2 ...

via the isocyanate. Isatoic anhydride is used as a blowing agent in the polymer industry, an application that exploits its tendency to release CO₂. Isatoic anhydride has also been reported to be used as a precursor for the synthesis of

methaqualone Methaqualone is a hypnotic sedative. It was sold under the brand names Quaalude ( ) and Sopor among others, which contained 300 mg of methaqualone, and sold as a combination drug under the brand name Mandrax, which contained 250 mg met ...

and related 4-quinazolinone based pharmaceutical drugs.A survey of reported syntheses of methaqualone and some positional and structural isomers Etienne F. van Zyl Forens. Sci. Int. 122, 142-149 (2001)

References

Carboxylic anhydrides