Isatoic Anhydride synthesis
- Product Name:Isatoic Anhydride
- CAS Number:118-48-9
- Molecular formula:C8H5NO3
- Molecular Weight:163.13
Yield:118-48-9 100%
Reaction Conditions:
in tetrahydrofuran at 45; for 12 h;
Steps:
1H-Benzo[d][1,3]oxazine-2,4-dion, (19).
Synthesis according to Darras,et al.4 2-Aminobenzoic acid (1.00 g, 7.29 mmol, 1.0 eq) was dissolved in dry THF (15 mL) before triphosgene (0.74 g, 2.48 mmol, 0.3 eq) was added. The mixture was heated over night at 45 °C. The solvent was removed and an off-white solid was obtained in quantitative yield. Analytical Data for C8H5NO3 (163.13 g/mol): Rf =0.47 (SiO2, petroleum ether/ethyl acetate 1:1, 2 drops triethylamine). Mp=176.6 - 179.2 °C. 1H-NMR (400 MHz, DMSO-d6, 300 K): δ= 11.76 (s, 1H, NH), 7.96 (d,J= 7.8 Hz, 1H, Ar-H), 7.83-7.73 (m, 1H, Ar-H), 7.29 (t,J= 7.6 Hz, 1H, Ar-H), 7.20 (d,J=8.2Hz, 1H, Ar-H) ppm. Spectral data is in accordance with the literature.4
References:
Wehle, Sarah;Espargaró, Alba;Sabaté, Raimon;Decker, Michael [Tetrahedron,2016,vol. 72,# 20,p. 2535 - 2543] Location in patent:supporting information
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