Isatoic anhydride

Names
Preferred IUPAC name

2H-3,1-Benzoxazine-2,4(1H)-dione

Identifiers

CAS Number

* 118-48-9 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL346059

ChemSpider |

* 8056

DrugBank |

* DB11593

EC Number |

* 204-255-0

PubChem CID

* 8359

UNII |

* R8TFA74Y4U Y

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

Tracking categories (test):

* SizeSet

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:

1. Tioperidone
2. Tranilast (actually made from acetanthranil)
3. Pelanserin
4. Diproqualone
5. Antrafenine
6. SJ-733
7. Nicafenine
8. Molinazone
9. Cloperidone
10. SGB 1534
11. U-29409 [31785-60-1]
12. Atolide

## 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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*[CID]: Compound ID
*[H317]: May cause an allergic skin reaction
*[H319]: Causes serious eye irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P321]: Specific treatment (see … on this label)
*[P501]: Dispose of contents/container to …