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CAS No. : | 847902-56-1 | MDL No. : | MFCD11878539 |
Formula : | C5H3FN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XCYLKKXQKCXJAE-UHFFFAOYSA-N |
M.W : | 158.09 | Pubchem ID : | 67387800 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With potassium carbonate; In acetonitrile; at 100℃; for 5.0h; | A mixture of <strong>[847902-56-1]5-fluoro-2-nitropyridin-3-ol</strong> (0.35 g, 2.2 mmol), ethyl iodide (1.4 mL, 18 MMOL), K2CO3 (3.0 g, 22 mmol), and acetonitrile (40 mL) was heated at 100 C under N2. After 5 h, the acetonitrile was removed in vacuo, and the residue was partitioned between water (200 ML) and chloroform (100 ML). The aqueous layer was extracted with chloroform (100 mL x 2), and the combined organic extracts were dried (MGS04), filtered, and concentrated to give 0.19 g of 3-ethoxy-5- FLUORO-2-NITROPYRIDINE. 1H NMR (CDC13, 500 MHz) 8 7.93 (dd, 2H), 7.22 (dd, 1H), 4.20 (q, 2H), 1.51 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sulfuric acid; nitric acid; at 0 - 20℃; | Example 10A 5-Fluoro-2-nitropyridin-3-ol With ice cooling, 5 g of 5-fluoropyridin-3-ol (44 mmol, 1 equivalent) were dissolved in 43 ml of concentrated sulphuric acid, and 2.8 ml of concentrated nitric acid were added at 0 C. over a period of 5 min. The reaction was warmed to RT and stirred overnight. The mixture was added to 100 g of ice and stirred for 30 min. The solid formed was filtered off and dried under reduced pressure. This gave 5.6 g (81% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method 1): Rt=0.45 min MS (ESneg): m/z=156.9 (M-H)- 1H NMR (400 MHz, DMSO-d6): delta=7.5 (dd, 1H); 8.08 (d, 1H); 12.2 (br. s, 1H). |
81% | With sulfuric acid; nitric acid; at 0 - 20℃; | Example 7A 5-Fluoro-2-nitropyridin-3-ol With ice cooling, 5 g of 5-fluoropyridin-3-ol (44 mmol, 1 equivalent) were dissolved in 43 ml of concentrated sulphuric acid, and, at 0 C., 2.8 ml of concentrated nitric acid were added over a period of 5 min. The reaction was warmed to RT, and stirring was continued overnight. The mixture was added to 100 g of ice and stirred for 30 min. The solid obtained was filtered off and dried under reduced pressure. This gave 5.6 g (81% of theory) of the title compound, which were used without further purification for the next reaction. LC-MS (Method 2): Rt=0.45 min MS (ESneg): m/z=156.9 (M-H)- 1H NMR (400 MHz, DMSO-d6): delta=7.5 (dd, 1H); 8.08 (d, 1H); 12.2 (br. s, 1H). |
81% | With sulfuric acid; nitric acid; at 0 - 20℃; | With ice cooling, 5 g of 5-fluoropyridin-3-ol (44mmol, 1 equivalent) were dissolved in 43 ml of concentratedsulphuric acid, and 2.8 ml of concentrated nitric acid wereadded at 00 C. over 5 mm. The reaction was warmed to RTand stirred overnight. The mixture was poured onto 100 g ofice and stirred for 30 mm. The crystals were filtered off withsuction and dried under reduced pressure. This gave 5.6 g(81% of theory) of the title compound which was usedwithout thrther purification for the next reaction.10347] LC-MS (Method 2): R=0.45 mm10348] MS (ESneg): mlz=156.9 (M-H)10349] ?H-NMR (400 MHz, DMSO-d5): oe=7.5 (dd, 1H);8.08 (d, 1H); 12.2 (br. s, 1H). |
Nitric acid (0.25 mL, 5.0 mmol) was added over 1 min to a solution of 5-fluoropyridin-3-ol (0.25 g, 2.2 mmol) and sulfuric acid (3 mL) at 70 C. After 20 min, a second aliquot (0.25 mL) of nitric acid was added over 1 min. After an additional 40 min, the reaction was cooled to 0 C. Water (25 mL) was added followed by slow addition of 10 N NAOH (13 mL) at 0 C. The solution was neutralized with 1 N HCI and concentrated to give 5-FLUORO-2-NITROPYRIDIN-3-OL. MS (ESI): 158. 8 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; for 16.0h; | Example 11A 2-Amino-5-fluoropyridin-3-ol 5.6 g of <strong>[847902-56-1]5-fluoro-2-nitropyridin-3-ol</strong> (Example 10A; 36 mmol) were dissolved in 2 l of ethanol, a catalytic amount of palladium on activated carbon (10%) was added and the mixture was hydrogenated under hydrogen standard pressure for 16 h. The mixture was filtered off through kieselguhr and the filtrate was concentrated (product batch 1). The residue was rinsed with methanol until the colour of the filtrate was no longer yellowish. The filtrate was concentrated, giving a second product batch. This gave a total of 4.26 g (85% of theory) of the title compound. LC-MS (Method 1): Rt=0.17 min MS (ESpos): m/z=128.9 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=5.4 (br. s, 2H); 6.8 (dd, 1H); 7.4 (d, 1H). |
85% | With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; for 16.0h; | Example 8A 2-Amino-5-fluoropyridin-3-ol 5.6 g of <strong>[847902-56-1]5-fluoro-2-nitropyridin-3-ol</strong> (Example 7A; 36 mmol) were dissolved in 2 l of ethanol, a catalytic amount of palladium on activated carbon (10%) was added and the mixture was hydrogenated under standard hydrogen pressure for 16 h. The mixture was filtered off through silica gel and the filtrate was concentrated (product batch 1). The filter cake was rinsed with methanol until the colour of the filtrate was no longer yellowish. The filtrate was concentrated, giving a second product batch. This gave 4.26 g (85% of theory) of the title compound. LC-MS (Method 2): Rt=0.17 min MS (ESpos): m/z=128.9 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=5.4 (br. s, 2H); 6.8 (dd, 1H); 7.4 (d, 1H). |
85% | With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; for 16.0h; | 5.6 g of <strong>[847902-56-1]5-fluoro-2-nitropyridin-3-ol</strong> (Example 7A;36 mmol) were dissolved in 2 1 of ethanol, a catalytic amount of palladium on activated carbon (10%) was added and the mixture was hydrogenated under 1 atmosphere of hydrogen for 16 h. The mixture was filtered off through kieselguhr, and the filtrate was concentrated. The filter cake was rinsed with methanol until the filtrate no longer had a yellow colout The filtrate was concentrated, giving a second product batch. Atotal of 4.26 g (85% of theory) of the title compound wereobtained.10352] LC-MS (Method 2): R=0.17 mm10353] MS (ESpos): mlz=128.9 (M+H)10354] ?H-NMR (400 MHz, DMSO-d5): &5.4 (bt 5, 2H);6.8 (dd, 1H); 7.4 (d, 1H). |
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