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CAS No. : | 36404-89-4 | MDL No. : | MFCD07698588 |
Formula : | C6H5NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DNTYEVWEOFZXFE-UHFFFAOYSA-N |
M.W : | 123.11 | Pubchem ID : | 7062196 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
20% | With copper(l) iodide; 8-quinolinol; potassium carbonate; In dimethyl sulfoxide; at 130℃; for 21h;Inert atmosphere; | Synthesis of 2-oxo- 1 -(4-(trifluoromethoxy)phenyl)- 1 ,2-dihydropyridine-3 - carbaldehyde (2-2) 2-oxo- l,2-dihydropyridine-3-carbaldehyde (200 mg, 1.63 mmdl), 1-iodo- 4-(trifluoromethoxy)benzene 2 (562 mg, 1.95 mmol), 8-hydroxyquinoline (47.2 mg, 0.324 mmol), copper iodide (61.9 mg, 0.324 mmol), and potassium carbonate (303 mg, 2.19 mmol) were combined in a round bottom flask with DMSO (3.5 mL) under a nitrogen atmosphere and heated to 130 C for 21 h. The reaction was cooled to room temperature and poured into a mixture of 10% aq. ammonium hydroxide and ethyl acetate. The resultant mixture was filtered through a pad bf Celite and washed with ethyl acetate three times. The layers were separated with the aqueous portion being back extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2S04, and concentrated in vacuo. Purification by flash column chromatography on silica gel (0 - 50% EtOAc in hexane) gave 92.0 mg (20%) of 2-2 as an off-white solid: 1H NMR (400 MHz, CDC13) δ 10.34 (1H, d, J= 0.8 Hz), 8.14 (1H, dd, J= 6.9, 2.3 Hz), 7.65 (1H, dd, J= 6.9, 2.3 Hz), 7.45 (2H, m), 7.38 (2H, m), 6.44 (1H, dt, J= 0.8, 6.9 Hz); ESI-MS m/z 284 [C13H8F3NO3 + H]+. |
20% | With copper(l) iodide; 8-quinolinol; potassium carbonate; In dimethyl sulfoxide; at 130℃; for 21h;Inert atmosphere; | 2-oxo-1,2-dihydropyridine-3-carbaldehyde 1-1 (200 mg, 1.63 mmol), <strong>[103962-05-6]1-iodo-4-(trifluoromethoxy)benzene</strong> 2-1 (562 mg, 1.95 mmol), 8-hydroxyquinoline (47.2 mg, 0.324 mmol), copper iodide (61.9 mg, 0.324 mmol), and potassium carbonate (303 mg, 2.19 mmol) were combined in a round bottom flask with DMSO (3.5 mL) under a nitrogen atmosphere and heated to 130 C for 21 h. The reaction was cooled to room temperature and poured into a mixture of 10% aq. ammonium hydroxide and ethyl acetate. The resultant mixture was filtered through a pad of Celite and washed with ethyl acetate three times. The layers were separated with the aqueous portion being back extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification by flash column chromatography on silica gel (0 - 50% EtOAc in hexane) gave 92.0 mg (20%) of 2-2 as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 10.34 (1H, d, J = 0.8 Hz), 8.14 (1H, dd, J = 6.9, 2.3 Hz), 7.65 (1H, dd, J = 6.9, 2.3 Hz), 7.45 (2H, m), 7.38 (2H, m), 6.44 (1H, dt, J = 0.8, 6.9 Hz); ESI-MS m/z 284 [C13H8F3NO3 + H]+. |
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