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CAS No. : | 104862-11-5 | MDL No. : | MFCD03407784 |
Formula : | C10H7NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 221.17 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a suspension of <strong>[10242-12-3]5-nitro-2-benzofurancarboxylic acid</strong> (5 g, 24.15 mmol) in CH2Cl2 (250 mL) at 0 C. was added DMF (0.100 mL) followed by (COCl)2 (2M in CH2Cl2, 36.23 mL, 72.46 mL) over a period of 10 min. The reaction was stirred at 0 C. for 1 h and then at room temperature for 30 min. The reaction solvent was removed under a reduced pressure, dried under high vacuum and again suspended in CH2Cl2 (250 mL). The solution was cooled to 0 C., were added pyridine (4.8 mL, 48.03 mmol) followed by McOH (10 mL, excess) and stirred overnight. The extractive work-up with CH2Cl2 gave the expected 2-methoxycarbonyl-5-nitrobenzofuran (R926609). 1H NMR (CDCl3): delta 8.66 (d, 1H, J=2.4 Hz), 8.36 (dd, 1H, J=2.4 and 9.6 Hz), 7.71 (d, 1H, J=9.3 Hz), 7.65 (s, 1H), 4.01 (s, 3H); LCMS: ret. time: 26.94 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In methanol; chloroform; | (a) 5-nitrobenzofuran-2-carboxylic Acid Methyl Ester. <strong>[10242-12-3]5-Nitrobenzofuran-2-carboxylic acid</strong> (10 g) was dissolved in methanol (200 mL) and chloroform (100 mL), and the mixture was cooled to 0 C. Under stirring conditions was bubbled HCl gas until the solution was saturated. The reaction mixture was stirred at room temperature overnight, and white solid was formed. The precipitate was collected by filtration to afford 9.5 g of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With 2-(Dimethylamino)pyridine; acetic anhydride; sodium sulfate;palladium-carbon; In water; ethyl acetate; acetone; | Methyl 5-acetaminobenzofuran-2-carboxylate (9). Methyl 5-nitrobenzofuran-2-carboxylate (13, 0.5 g, 2.26 mmol, made from <strong>[10242-12-3]5-nitrobenzofuran-2-carboxylic acid</strong>, Trans World Chemicals, Inc.) was dissolved in ethyl acetate (40 mL) and 5% Pd/C (30 mg) was added. The reaction mixture was hydrogenated for 1 h at room temperature at a pressure of 60 lb/inch2. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was dissolved in acetone (10 mL) and was used without further purification. Acetic anhydride (0.86 mL, 9.1 mmol) and dimethylaminopyridine (20 mg) was added. The solution was stirred for 1 h at room temperature. Water (20 mL) was added and the mixture was extracted with ethyl acetate (40 mL*5). The solution was dried using sodium sulfate and solvent was removed in vacuo. A grey powder 9 was obtained (321 mg, 61% yield). An analytical sample was recrystallized in ethyl acetate. mp: 158-159 C. 1 H NMR (DMSO-d6, ppm): 10.03 (s, 1 H, NH), 8.19-8.18 (d, 1 H, J=1.6 Hz, Ar--H), 7.76-7.75 (d, 1 H, J=1.1 Hz, Ar--H), 7.65-7.63 (d, 1 H, J=9.0 Hz, Ar--H), 7.55-7.52 (dd, 2 H, J=2.3, 8.9 Hz, Ar--H), 3.89 (s, 1 H, OCH3), 2.07 (s, 3 H, CH3 CO), Anal. (C12 H11 NO4), C, H, N. |