Английская Википедия:Isatoic anhydride
Шаблон:Chembox 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]
References
