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Isatoic anhydride

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Isatoic anhydride
Names
Preferred IUPAC name 2H-3,1-Benzoxazine-2,4(1H)-dione
Identifiers
CAS Number
ECHA InfoCard 100.003.869 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
Properties
Chemical formula C8H5NO3
Molar mass 163.132 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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

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. 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:

  1. Tioperidone
  2. Tranilast
  3. Pelanserin
  4. Diproqualone
  5. Antrafenine
  6. SJ-733
  7. Nicafenine
  8. Molinazone
  9. Cloperidone
  10. SGB 1534

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". Forensic Sci. Int. 122 (2–3): 142–149. doi:10.1016/S0379-0738(01)00484-4. PMID 11672968.
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