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.[1]

Isatoic anhydride
Identifiers
ECHA InfoCard 100.003.869
UNII
Properties
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

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.

Isatoic anhydride has also been reported to be used as a precursor for the synthesis of methaqualone and related 4-quinazolinone based pharmaceutical drugs.[3]

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gollark: After not mentioning this in your campaign, if I remember right.
gollark: I don't know. I don't think it's a significant amount but I don't have metrics on how often:- there actually is something like that going on/obviously visible, and nothing else happening in non-off-topic channels people actually discuss esolangs in- this is likely to make someone who may otherwise be an active member not be (I'd expect this is driven by other things)

References

  1. E. C. Wagner, Marion F. Fegley. (1947). "Isatoic anhydride". Org. Synth. 27: 45. doi:10.15227/orgsyn.027.0045.CS1 maint: uses authors parameter (link)
  2. Coppola, Gary M. (1980). "The Chemistry of Isatoic Anhydride". Synthesis. 7: 505–36. doi:10.1055/s-1980-29110.
  3. A survey of reported syntheses of methaqualone and some positional and structural isomers Etienne F. van Zyl Forens. Sci. Int. 122, 142-149 (2001)
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