Isatoic anhydride

Names
Preferred IUPAC name

2H-3,1-Benzoxazine-2,4(1H)-dione

Identifiers

CAS Number

* 118-48-9 Y

PubChem CID

* 8359

UNII |

* R8TFA74Y4U Y

Properties

Chemical formula

| C8H5NO3
Molar mass | 163.132 g·mol−1
Appearance  | white solid
Melting point |  243 °C (469 °F; 516 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Isatoic anhydride is an organic compound derived from anthranilic acid. A white solid, it is prepared by reaction of anthranilic acid with phosgene.[1]

## 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 hydroxyquinolinone derivatives. Deprotonation followed by alkylation gives the N-substituted derivatives. Sodium azide gives the benzimidazolone via the isocyanate.[2] Isatoic anhydride is used as a blowing agent in the polymer industry, an application that exploits its tendency to release CO2.

## Uses

Isatoic anhydride has been used as a precursor for the synthesis of methaqualone and related 4-quinazolinone-based pharmaceutical drugs, including:[3]

* Tioperidone
* Tranilast
* Pelanserin
* Diproqualone
* Antrafenine
* SJ-733
* Nicafenine
* Molinazone
* Cloperidone

## References

1. ↑ E. C. Wagner; Marion F. Fegley. (1947). "Isatoic anhydride". Org. Synth. 27: 45. doi:10.15227/orgsyn.027.0045.
2. ↑ Coppola, Gary M. (1980). "The Chemistry of Isatoic Anhydride". Synthesis 7 (7): 505–36. doi:10.1055/s-1980-29110.
3. ↑ Etienne F. van Zyl (2001). "A survey of reported syntheses of methaqualone and some positional and structural isomers". Forens. Sci. Int. 122: 142-149.

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*[CID]: Compound ID