Isatoic anhydride

Isatoic anhydride
Names
	Preferred IUPAC name 2H-3,1-Benzoxazine-2,4(1H)-dione
Identifiers
CAS Number	118-48-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL346059;
ChemSpider	8056;
DrugBank	DB11593;
EC Number	204-255-0;
PubChem CID	8359;
UNII	R8TFA74Y4U ;
	InChI InChI=1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11) Key: TXJUTRJFNRYTHH-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)C(=O)OC(=O)N2;
Properties
Chemical formula	C8H5NO3
Molar mass	163.132 g·mol−1
Appearance	white solid
Melting point	243 °C (469 °F; 516 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H317, H319
GHS precautionary statements	P261, P264+265Script error: No such module "Preview warning".Category:GHS errors, P272, P280, P302+352, P305+351+338, P321, P333+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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^[3] and related 4-quinazolinone-based pharmaceutical drugs, including:

Tioperidone
Tranilast
Pelanserin
Diproqualone
Antrafenine
SJ-733
Nicafenine
Molinazone
Cloperidone
SGB 1534

References

↑ E. C. Wagner; Marion F. Fegley. (1947). "Isatoic anhydride". Org. Synth. 27: 45. doi:10.15227/orgsyn.027.0045.
↑ Coppola, Gary M. (1980). "The Chemistry of Isatoic Anhydride". Synthesis 7 (7): 505–36. doi:10.1055/s-1980-29110.
↑ 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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[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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Isatoic anhydride

Topic: Chemistry

Reactions

Uses

References