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Isatoic anhydride

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:

C<sub>6</sub>H<sub>4</sub>C<sub>2</sub>O<sub>3</sub>NH + ROH → C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>R)(NH<sub>2</sub>) + CO<sub>2</sub>

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 CO<sub>2</sub>.

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
  11. U-29409 [31785-60-1]

References