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CAS No. : | 19235-88-2 | MDL No. : | MFCD00191627 |
Formula : | C6H3N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ONDDYTHSSNTDLR-UHFFFAOYSA-N |
M.W : | 149.11 | Pubchem ID : | 568650 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P310-P321-P330-P332+P313-P362-P403+P233-P405-P501 | UN#: | 2811 |
Hazard Statements: | H301-H315-H318-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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 |
---|---|---|
100% | With chloro-trimethyl-silane; water; at 20℃; for 1h; | 4-Nitropicolinonitrile (100 mg, 0.67 mmol), chlorotrimethylsilane (0.17 mL, 1.4 mmol) and H2O (0.024 mL, 1.4 mmol) was sonicated in a sonicator at rt for 1.0 h. It was diluted with EtOAc, washed with NaHCO3, brine and dried over Na2SO4. After removal of solvent, 99A (134 mg, 100% yield) was obtained as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 8.29 (dd, J=5.27, 2.20 Hz, 1H) 8.74 (d, J=2.20 Hz, 1H) 8.98 (d, J=5.27 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.1% | With sodium sulfite; In ice-water; sulfuric acid; water; | III-2-2: Synthesis of 4-nitropicolinic acid A solution of 5.00 g (34 mmol) of 2-cyano-4-nitropyridine dissolved in 50 g of 90% sulfuric acid was stirred at 120 C. for 2 hours. Then, at 20 to 25 C., a solution of 5.60 g of sodium sulfite in 10 ml of water was dropwise added, and the mixture was stirred at the same temperature for one hour, and further, at 80 C. for one hour under heating. After cooling, 100 g of ice-water was added, and the mixture was adjusted to a pH of about 2 with sodium carbonate. The mixture was left to stand in a refrigerator, resulting in precipitation of the solid. The solid was collected by filtration and recrystallized from a water-acetone mixture to obtain 3.50 g of pale yellow crystals (yield 62.1%). m.p.: 157-158 C. (decompd.). IR (KBr): 1710, 1600, 1585, 1535 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 0.583333h; | 4-nitropicolinonitrile B.39 (5 g, 33.5 mmol) in 64 mL DMF was stirred at room temperature as 67 mL TBAF (1 M in THF, 67 mmol) was added. After 35 minutes, the reaction was poured into 500 mL 1 : 1 ethyl acetate-water. The organic layer was washed with water and brine, dried over Na2SO4 and condensed. The orange-brown residue was purified by flash chromatography (0-10-100% ethyl acetate in hexane) to give 4-fluoropicolinonitrile B.40 (2.78 g, 68%). IH NMR (500 MHz, CHLOROFORM-d) δ ppm 8.72 (1 H, dd, J=7.9, 5.7 Hz), 7.48 (1 H, dd, J=8.1, 2.4 Hz), 7.30 (1 H, ddd, J=8.1, 5.6, 2.4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23.0% | In water; | III-2-1: Synthesis of 2-cyano-4-nitropyridine A mixture of 20.0 g (0.14 mol) of 4-nitropyridine N-oxide and 18.0 g (0.14 mol) of dimethylsulfuric acid was stirred at 65 to 70 C. for 2 hours, and then left to stand in a refrigerator overnight, whereby solidification occurred. The solid was dissolved in 50 ml of water, and a solution of 14.6 g (0.3 mol) of sodium cyanide in 100 ml of water was dropwise added with vigorous stirring under a nitrogen atmosphere at -7 to -8 C., followed by stirring at the same temperature for 7 hours. After standing at room temperature overnight, the precipitates were collected by filtration, washed with water, dried and recrystallized from isopropyl ether to give 4.90 g of yellow crystals (yield 23.0%). m.p.: 70.0-71.0 C. IR (KBr): 2240, 1600, 1575 cm-1. |
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