ChemicalBook CAS DataBase List Isatoic Anhydride

Isatoic Anhydride synthesis

12synthesis methods

Product Name:Isatoic Anhydride
CAS Number:118-48-9
Molecular formula:C8H5NO3
Molecular Weight:163.13

Phosphorus tribromide (0.035 mol) was added to a solution of N-carbethoxy- or N-carbobenzoxy-anthranilic acid (0.1 mol;prepared by coupling anthranilic acid with the corresponding carbalkoxy chloride in the usual way) in anhydrous diethyl ether (100 mL). After 24 h at room temperature, isatoic anhydride had separated as a microcrystalline product. It was collected by filtration, washed with dry diethyl ether, and recrystallized from ethanol. Yield ca. 90%.

32315-10-9 Synthesis

32315-10-9
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118-92-3
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118-48-9
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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): R_f=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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