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CAS No. : | 49609-15-6 | MDL No. : | MFCD13192242 |
Formula : | C10H8ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FOARXBSDMBUBEG-UHFFFAOYSA-N |
M.W : | 193.63 | Pubchem ID : | 12415558 |
Synonyms : |
|
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 |
---|---|---|
98% | for 3 h; Reflux | 300 mg (1.9 mmol) of 7-methoxyquinolin-2(1H)-one was dissolved in 1.1 mL of POCl3 (12 mmol) and heated at reflux for 3 h. The mixture was poured into iced water, neutralized with sat NaHCO3 and extracted with ethyl acetate. Yield 98percent.1H NMR (400 MHz, CDCl3) δ 8.01 (d, J = 8.5 Hz, 1H), 7.68 (d, J = 8.9 Hz, 1H), 7.35 (d, J = 2.4 Hz, 1H), 7.25 (d, J = 8.3 Hz, 1H), 7.20 (dd, J = 8.9, 2.5 Hz, 1H), 3.93 (s, 3H). |
66% | With N-ethyl-N,N-diisopropylamine; trichlorophosphate In toluene at 120℃; for 4 h; | [00222] 7-methoxyquinolin-2(lH)-one (3.5 g, 20 mmol) was dissolved in toluene (80 mL), then phosphoryl trichloride (6.1 g, 40 mmol) and diisopropylethylamine (5.2 g, 40 mmol) were added to the mixture which was heated to 120 °C for 4 h, concentrated, and extracted with dichloromethane (100 mL x 2). The combined organic layers were washed with saturated sodium bicarbonate, brine, dried, concentrated under reduced pressure, and purified by flash chromatography eluting with petroleum ether: ethyl acetate (1 :5) to afford the title compound as a red solid (2.55 g, 66 percent). MS (ESI): m/z 194 [M + H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12 h; | Intermediate 441 (2.5 g, 13.9 mmol, 1 .0 eq ) was dissolved in DMF (25 mL), 2CO3 (5.76 g, 4 1 .76 mmol, 3 eq ) and CH3I (5.2 g, 36.6 mmol, 2.63 eq ) were added. The reaction mi ture w as stirred at 25°C for 1 2 hr.. The reaction mi ture was poured into water ( 100 ml. ) and was extracted with EtOAc ( 1 50 mL ). The organic layer was washed by water (80 mL x 2 ), brine (800 mL ) and dried over anhydrous Na2SC<4. The solvent was removed under reduced pressure to give intermediate 442 (2.6 g, 96percent yield ) as a white solid. |
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