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| | 1,3-Dioxo-2-isoindolineaceticacid Basic information |
| Product Name: | 1,3-Dioxo-2-isoindolineaceticacid | | Synonyms: | N-(1,3-Dihydro-1,3-dioxoisobenzofuran-4-yl)acetamide;AcetaMide, N-(1,3-dihydro-1,3-dioxo-4-isobenzofuranyl)-;3-AcetylaMino-phthalsaeure-anhydrid;1,3-Dioxo-2-isoindolineaceticacid CAS:6296-53-3;N-(1,3-Dioxo-1,3-dihydro-2-benzofuran-4-yl)acetaMide;NSC 16261;NSC 17048;N-(1,3-Dioxo-4-isobenzofuranyl)acetaMide | | CAS: | 6296-53-3 | | MF: | C10H7NO4 | | MW: | 205.17 | | EINECS: | 808-040-8 | | Product Categories: | | | Mol File: | 6296-53-3.mol |  |
| | 1,3-Dioxo-2-isoindolineaceticacid Chemical Properties |
| Melting point | 185-186℃ | | Boiling point | 489.1±28.0 °C(Predicted) | | density | 1.512±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform (Slightly, Sonicated), Ethyl Acetate (Slightly, Sonicated), Methanol | | form | Solid | | pka | 13.81±0.20(Predicted) | | color | Off-White to Pale Yellow | | Stability: | Moisture Sensitive | | InChI | InChI=1S/C10H7NO4/c1-5(12)11-7-4-2-3-6-8(7)10(14)15-9(6)13/h2-4H,1H3,(H,11,12) | | InChIKey | PAUAJOABXCGLCN-UHFFFAOYSA-N | | SMILES | C(NC1=CC=CC2C(=O)OC(=O)C1=2)(=O)C |
| | 1,3-Dioxo-2-isoindolineaceticacid Usage And Synthesis |
| Uses | 3-Acetylaminophthalic Anhydride is used in the synthesis of Apremilast, a potent phosphodiesterase 4 and tumor necrosis Factor-α inhibitor used in the treatment of psoriatic arthritis. Also a reagent in the preparation of Tillivalline. Apremilast Impurity 2 | | Synthesis | General procedure for the synthesis of N-(1,3-dioxo-1,3-dihydroisobenzofuran-4-yl)acetamide from 3-nitrophthalic acid and acetic anhydride: 3-nitrophthalic acid (100.0 g) and acetic anhydride (1 L) were added to a hydrogenation kettle and heated to 80 °C until the raw materials were completely dissolved. Subsequently, the reaction mixture was cooled to room temperature and 10% Pd/C catalyst (3 g) was added. The atmosphere in the reaction kettle was replaced twice with nitrogen, then hydrogen was introduced to a pressure of 1 MPa, and the reaction was kept at room temperature until hydrogen absorption stopped. Upon completion of the reaction, the hydrogen was vented and the reactor was purged with nitrogen. Next, the reaction mixture was heated to 110-115 °C until the feedstock or intermediate completely disappeared. Thermal filtration was carried out and the filtrate was cooled to 0-5 °C, the product was collected by filtration and washed with glacial acetic acid. A final light yellow crystalline product of 80.6 g was obtained with 83% yield and 99.0% HPLC purity. | | References | [1] Patent: CN105294534, 2016, A. Location in patent: Paragraph 0036; 0037 |
| | 1,3-Dioxo-2-isoindolineaceticacid Preparation Products And Raw materials |
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