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CAS No. : | 529-37-3 | MDL No. : | MFCD00006777 |
Formula : | C9H7NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PMZDQRJGMBOQBF-UHFFFAOYSA-N |
M.W : | 145.16 g/mol | Pubchem ID : | 69141 |
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: |
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* 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 |
---|---|---|
97.9% | With polyphosphoric acid; at 100℃; | The compound 1 obtained in the previous step was mixed with 40 mL of polyphosphoric acid (PPA), and the reaction was stirred at 100 C for 1-2 hours. The end of the reaction was monitored by TLC. After the reaction was completed, the reaction solution was poured into 200 mL of ice water, and the pH was adjusted with sodium carbonate. = 5-6, extracted with 250 * 2 mL of ethyl acetate, combined organic layers, dried over anhydrous sodium sulfate, and concentrated the filtrate under reduced pressure to obtain a pale yellow solid compound 2 (14.22 g, 97.9%, HPLC: 98.65%); |
14.22 g | With polyphosphoric acid; at 100℃; | The compound 1 obtained in the previous step was mixed with 40 mL of polyphosphoric acid (PPA), and the reaction was stirred at 100 C for 1-2 hours. The end of the reaction was monitored by TLC. After the reaction was completed, the reaction solution was poured into 200 mL of ice water and the pH was adjusted with sodium carbonate = 5-6, extracted with 250 * 2 mL of ethyl acetate, combined organic layers, dried over anhydrous sodium sulfate, and concentrated the filtrate under reduced pressure to obtain a pale yellow solid compound 2 (14.22 g, 97.9%, HPLC: 98.65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In diphenylether; at 250℃; for 0.5h;Inert atmosphere; | Diphenylether (140 mL) was heated to 250 C and stirred vigorously under nitrogen atmosphere. 5-Anilinomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione (6) (26.30 g, 0.11 mol) was added portionwise at the same temperature, and the reaction mixture was stirred for 30 min. The resulting solution was allowed to cool to 70 C and diluted with n-hexane (200 mL). The precipitate was filtered off, washed with n-hexane, and dried in vacuo. The title compound was obtained as a brown solid (14.26 g, 92%), mp 200-202 C (lit., 28 mp 199-203 C); 1H NMR (DMSO-d6, 400 MHz) delta 11.72 (br s, 1H), 8.08 (dd, 1H, J=0.8, 8.0 Hz), 7.88 (d, 1H, J=7.2 Hz), 7.66-7.60 (m, 1H), 7.53 (d, 1H, J=8.4 Hz), 7.34-7.27 (m, 1H), 6.02 (d, 1H, J=7.6 Hz); 13C NMR (DMSO-d6, 400 MHz) delta 176.7, 139.8, 139.2, 131.5, 125.7, 124.8, 122.9, 118.1, 108.6; C9H7NO (145.16); LCMS (ESI+) m/z 146 [M+H]+. Anal. Calcd for C9H7NO (145.16) C, 74.47; H, 4.86; N, 9.65. Found: C, 74.19; H, 4.84; N, 9.68. |
90% | at 80℃; for 2h;Ionic liquid; Inert atmosphere; | (b) Typical experimental procedure for the cyclization of 4a-e: Compound 4a-e (5 mmol) and [BMIM]BF4/OTf (3 mL) were taken in a round bottomed flask having provision to carry out the reaction under nitrogen atmosphere. The contents of the flask were stirred magnetically at 80 +/- 2 C. The progress of the reaction was monitored on a TLC plate in pet.ether-ethyl acetate (8:2). After completion of the reaction, the product was extracted with ethyl acetate (3 × 10 mL). The solvent was recovered under reduced pressure (5 mm of Hg). The pasty mass thus obtained was extracted with diethyl ether (3 × 10 mL), dried over anhydrous sodium sulphate and ether was distilled. The product so obtained was purified by crystallization with ethanol/column chromatography (Merck Silica gel 60-120 mesh) and eluting TLC product with pet.ether-ethylacetate (8:2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With palladium 10% on activated carbon; cyclohexene; In ethanol; water; for 2h;Inert atmosphere; Reflux; | 2. Synthesis of intermediate 056-4 The intermediate 056-2 (75.6 g, 34.5 mmol) was dissolved in 100 mL of anhydrous ethanol in a 250 mL three-necked flask at room temperature under a nitrogen atmosphere, followed by adding cyclohexene (the intermediate 056-3) (14.2 g, 172.9 mmol) and palladium on carbon containing water (18.7 g, 10% Pd) into the reaction system at room temperature. The reaction was heated to reflux for 2 h. After the reaction was completed, the mixture was cooled to room temperature and then filtered by suction. The filtrate was collected and concentrated to dryness. The residue was washed with 100 mL of the mixed solvent (EA/PE = 1: 2) once. The solid was filtered by suction, and the filter cake was dried to give 4.2 g of the intermediate 056-4 (84%) as a yellow solid. LCMS: 146.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With sodium hydroxide; In methanol; water; | EXAMPLE 21 3-Hydroxy-2-phenyl-4H-1-benzopyridin-4-one To a solution of 0.23 g (0.96 mmol) 3-hydroxy-2-phenyl-2H, 3H, 4H-1-benzopyridin-4-one, 0.94 g NaOH (in 4 mL water) and 35 mL MeOH was added 15 mL of H2 O2 over ice bath. The yellow solution was then stirred at room temperature for 4 hours before the mixture was poured into 300 mL of water. The resulting mixture was extracted with CH2 Cl2 and the solvent was removed from the organic phase. The resulting residue was recrystallized form toluene which gave the desired product in 17% yield. MP: 260-262 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formaldehyd; In ethyl acetate; | A mixture of the 4(1H)-quinolone (41.1 g), 40% formaldehyde solution (60 ml), and 1 molar sodium hydroxide solution (360 ml) was allowed to stand for seventy two hours at 35 C. The reaction mixture was then neutralised with glacial acetic acid (21.6 g) and the solution extracted continuously with ethyl acetate (800 ml) for 6 hours. Three crops, shown by NMR and t.l.c. to be identical and the required product, 3-hydroxymethyl-4-(1H)-quinolone, were filtered off. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With hydrogenchloride; sodium methylate; In 1,4-dioxane; chloroform; water; | Example 2 Process for Producing 4-Quinolone 2-Aminoacetophenone (7.0 g, 52 mmol) was added to and dissolved in 1,4-dioxane (100 ml). To the solution obtained was added sodium methoxide (8.4 g, 156 mmol), and the mixture was stirred at room temperature for 30 minutes. Ethyl formate (21 ml, 261 mmol) was then added, and the mixture was stirred at room temperature for an additional 125 minutes. After adding water (5 ml) to the reaction solution, and stirring for 10 minutes, 10% hydrochloric acid was added to the mixture for neutralization. The reaction solution was then concentrated under reduced pressure. The residue was suspended in chloroform (100 ml), collected by filtration, washed with chloroform (100 ml), and then purified by silica gel column chromatography to give 4.5 g of the desired compound (yield 60%). 1H-NMR (DMSO-d6, 400 MHz): delta 6.02 (d, J=7.6 Hz, 1H), 7.30 (m, 1H), 7.53 (d, J=8.1 Hz, 1H), 7.63 (m, 1H), 7.89 (dd, J=6.1 Hz, 7.3 Hz, 1H), 8.08 (dd, J=1.5 Hz, 8.1 Hz, 1H), 11.74 (brs, 1H). Mass Spectrometry (FD-MS, m/z): 145 (M30). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; for 3h; | To a stirred solution of 1H-quinolin-4-one (7) (10.00 g, 68.89 mmol) in DMF (100 mL) N-iodosuccinimide (16.74 g, 74.40 mmol) was added portionwise at room temperature. The reaction mixture was stirred for 3 h. The solvent was evaporated and the residue was boiled in water (100 mL). The precipitate was filtered off, washed with water, and dried in vacuo. The title compound was obtained as a beige solid (16.92 g, 91%), mp 296-298 C (lit., 29 mp 296-299 C); 1H NMR (DMSO-d6, 400 MHz) delta 12.18 (br s, 1H), 8.50 (d, 1H, J=6.4), 8.11 (d, 1H, J=8.0 Hz), 7.72-7.65 (m, 1H), 7.59 (d, 1H, J=8.0 Hz), 7.42-7.35 (m, 1H); 13C NMR (DMSO-d6, 400 MHz) delta 172.9, 144.5, 139.3, 131.8, 125.3, 124.0, 122.3, 118.3, 80.5; C9H6INO (271.06); LCMS (ESI+) m/z 272 [M+H]+. Anal. Calcd for C9H6INO (271.06) C, 39.88; H, 2.23; N, 5.17. Found: C, 39.73; H, 2.22; N, 5.18. |
lH-Quinolin-4-one (2.90 g, 20 mmol, 1 equiv) in 5 mL of DMF was treated with 1.12 g of KOH (2 equiv) and 5.30 g of iodine (1.05 equiv) for 2 hours. The reaction was quenched by slow addition of saturated aqueous solution of Na2S2theta3. Filtration gave 3-iodo- lH-quinolin-4-one as an off-white solid. | ||
1.33 g | With iodine; sodium carbonate; In methanol; at 20℃; | A mixture of 1.40 g 2-aminoacetophenone (5, 10.37 mmol) and 2.0 cm3 dimethylformamide dimethylacetal (DMFDMA,15.12 mmol) in 20 cm3 toluene was heated at 95 C for 3 h. The reaction was then cooled at room temperature. The excess of the solvent was evaporated under vacuum using rotavapor and the residue was recrystallized from EtOAc-hexane to give quinolin-4(1H)-one 6 as a yellow solid (1.24 g, 75%). To a solution of compound 6 in 20 cm3 MeOH, 2.05 g iodine (8.72 mmol) as solid and 0.92 g Na2CO3 (8.72 mmol) were added. The reaction mixture was allowed to stir overnight at room temperature. A solution of saturated aqueous sodium thiosulfate (10 cm3) was added and the mixture was extracted by CHCl3 (3 9 50 cm3). The organic solution was dried(Na2SO4), filtered and evaporated under reduced pressure.The resulting crude product was purified by column chromatography (silica gel, hexane:EtOAc, 1:1) to afford 3-iodoquinolin-4(1H)-one (6) as yellow solid (1.33 g,56%). M.p.: 216-218 C (Lit. [21] 217-218 C); the 1HNMR spectrum was identical to that given in [21]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | The stirred solution of 1H-quinolin-4-one (7) (15.00 g, 0.10 mol) in acetic acid (90 mL) was refluxed for 10 min and bromine (16.51 g, 0.10 mol) was added dropwise at the same temperature. The reaction mixture was stirred for 2 h, then it was allowed to cool to room temperature. The resulting suspension was poured on crushed ice (340 mL) and diluted further with sodium thiosulfate solution (1 N, 50 mL). The resulting precipitate was filtered off, washed with water and dried in vacuo. The title compound was obtained as a beige solid (22.94 g, 99%), mp 199-201 C (lit., 30 mp 278-279 C); 1H NMR (DMSO-d6, 400 MHz) delta 12.27 (br s, 1H), 8.47 (d, 1H, J=6.4 Hz), 8.14 (dd, 1H, J=0.8, 8.0 Hz), 7.72-7.66 (m, 1H), 7.60 (d, 1H, J=8.0 Hz), 7.42-7.36 (m, 1H); 13C NMR (DMSO-d6, 400 MHz) delta 171.2, 140.0, 139.1, 131.8, 125.1, 124.1, 123.9, 118.4, 104.0; C9H6BrNO (224.06); LCMS (ESI+) m/z 224, 226 [M+H]+. Anal. Calcd for C9H6BrNO (224.06) C, 48.25; H, 2.70; N, 6.25. Found: C, 48.08; H, 2.69; N, 6.27. | |
91.3% | With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 80℃; | Compound 2 (10.00g, 68.87mmol, 1.00eq) and N-bromosuccinimide (14.71g, 82.64mmol, 1.20eq) were dissolved in 60mL DMF, and the reaction was stirred at 80 C for 3-5h. The reaction was monitored by TLC At the end of the reaction, after the reaction was completed, most of the DMF was removed by concentration under reduced pressure. The residue was added with 100 mL of water and extracted twice with 150 * 2 mL of ethyl acetate. The organic layers were combined, and the organic layer was washed once with 200 mL of saturated saline. After drying over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a yellow solid compound 3 (14.10 g, 91.3%, HPLC: 95.41%); |
91.3% | In N,N-dimethyl-formamide; at 80℃; | Compound 2 (10.00g, 68.87mmol, 1.00eq) and N-bromosuccinimide (14.71g, 82.64mmol, 1.20eq) were dissolved in 60mL DMF, and the reaction was stirred at 80 C for 3-5h. The reaction was monitored by TLC At the end of the reaction, after the reaction was completed, most of the DMF was removed by concentration under reduced pressure. The residue was added with 100 mL of water and extracted twice with 150 * 2 mL of ethyl acetate. The organic layers were combined, and the organic layer was washed once with 200 mL of saturated saline. After drying over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a yellow solid compound 3 (14.10 g, 91.3%, HPLC: 95.41%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation; | General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation; | General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation; | General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation; | General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation; | General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation; | General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | 3. Synthesis of intermediate 056-5 Under a nitrogen atmosphere, the intermediate 056-4 (3.0 g, 20.7 mmol) as a raw material was dissolved in 50 mL of N,N-dimethylformamide (DMF) in a 100 mL single-necked flask at room temperature, and then the reaction system was cooled to 0C and NaH (65%, dispersed in a mineral oil) (2.3 g, 95.8 mmol) was added thereto. The reaction was maintained at 0C for 30 min. Next, 2,4-dichloropyrimidine (the intermediate 001-5) (6.0 g, 40.3 mmol) was dissolved in 50 mL of DMF and the resulting solution was added dropwisely to the reaction system at 0C. The reaction was carried out at 0C for 2h until the reaction was detected to confirm the reaction was completed. The reaction mixture was poured into 100 mL of aqueous solution of saturated ammonium chloride to quench the reaction, and the system was extracted with 100 mL of ethyl acetate three times. The organic phases were combined, washed with 100 mL of saturated brine three times, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by flash column chromatography (column: silica gel; mobile phase: ethyl acetate/petroleum ether; 50% ethyl acetate to 85% ethyl acetate; 30 min; detection wavelength: 254 nm) to give 1 g of the intermediate 056-5 (19%) as a white solid. LCMS: 258.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With ammonium iodide; In N,N-dimethyl-formamide; at 135℃; for 12h; | General procedure: 0.5 mL DMF was added into the flask charged with 0.25 mmol of flavones, 0.25 mmol of diaryl diselenides, NH4I (1.25 mmol). The mixture was stirred at 135 C for 12 hours, then cooled down to room temperature, diluted with 20 mL ethyl acetate and washed with 10 mL H2O. The aqueous layer was extracted twice with ethyl acetate (5 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents the residue was purified by flash column chromatography (silica gel, PE/EtOAc=10:1) to afford the desired products 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With ammonium iodide; In N,N-dimethyl-formamide; at 135℃; for 12h; | General procedure: 0.5 mL DMF was added into the flask charged with 0.25 mmol of flavones, 0.25 mmol of diaryl diselenides, NH4I (1.25 mmol). The mixture was stirred at 135 C for 12 hours, then cooled down to room temperature, diluted with 20 mL ethyl acetate and washed with 10 mL H2O. The aqueous layer was extracted twice with ethyl acetate (5 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents the residue was purified by flash column chromatography (silica gel, PE/EtOAc=10:1) to afford the desired products 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In toluene; at 95℃; for 3h; | A mixture of 1.40 g 2-aminoacetophenone (5, 10.37 mmol) and 2.0 cm3 dimethylformamide dimethylacetal (DMFDMA,15.12 mmol) in 20 cm3 toluene was heated at 95 C for 3 h. The reaction was then cooled at room temperature. The excess of the solvent was evaporated under vacuum using rotavapor and the residue was recrystallized from EtOAc-hexane to give quinolin-4(1H)-one 6 as a yellow solid (1.24 g, 75%). To a solution of compound 6 in 20 cm3 MeOH, 2.05 g iodine (8.72 mmol) as solid and 0.92 g Na2CO3 (8.72 mmol) were added. The reaction mixture was allowed to stir overnight at room temperature. A solution of saturated aqueous sodium thiosulfate (10 cm3) was added and the mixture was extracted by CHCl3 (3 9 50 cm3). The organic solution was dried(Na2SO4), filtered and evaporated under reduced pressure.The resulting crude product was purified by column chromatography (silica gel, hexane:EtOAc, 1:1) to afford 3-iodoquinolin-4(1H)-one (6) as yellow solid (1.33 g,56%). M.p.: 216-218 C (Lit. [21] 217-218 C); the 1HNMR spectrum was identical to that given in [21]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dipotassium peroxodisulfate; iodine; In acetonitrile; at 80℃; | General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; at 20℃; for 16h; | General procedure: To a suspension of 4-quinolones (4. 0 mmol, 1. 0 equiv) and potassium hydroxide (1.5 equiv) in methanol (4 mL) was added alkyl halide (10.0 equiv). The reaction mixture was stirred at room temperature for 16 h. Upon completion, the suspension was washed with ethyl acetate (20 mL) and water (20 mL), then organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting organic residue was purified by flash chromatography column over silica gel (SiO2) to afford the alkylated quinolone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; at 20℃; for 16h; | General procedure: To a suspension of 4-quinolones (4. 0 mmol, 1. 0 equiv) and potassium hydroxide (1.5 equiv) in methanol (4 mL) was added alkyl halide (10.0 equiv). The reaction mixture was stirred at room temperature for 16 h. Upon completion, the suspension was washed with ethyl acetate (20 mL) and water (20 mL), then organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting organic residue was purified by flash chromatography column over silica gel (SiO2) to afford the alkylated quinolone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; at 20℃; for 16h; | General procedure: To a suspension of 4-quinolones (4. 0 mmol, 1. 0 equiv) and potassium hydroxide (1.5 equiv) in methanol (4 mL) was added alkyl halide (10.0 equiv). The reaction mixture was stirred at room temperature for 16 h. Upon completion, the suspension was washed with ethyl acetate (20 mL) and water (20 mL), then organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting organic residue was purified by flash chromatography column over silica gel (SiO2) to afford the alkylated quinolone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; at 20℃; for 16h; | General procedure: To a suspension of 4-quinolones (4. 0 mmol, 1. 0 equiv) and potassium hydroxide (1.5 equiv) in methanol (4 mL) was added alkyl halide (10.0 equiv). The reaction mixture was stirred at room temperature for 16 h. Upon completion, the suspension was washed with ethyl acetate (20 mL) and water (20 mL), then organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting organic residue was purified by flash chromatography column over silica gel (SiO2) to afford the alkylated quinolone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; at 20℃; for 16h; | General procedure: To a suspension of 4-quinolones (4. 0 mmol, 1. 0 equiv) and potassium hydroxide (1.5 equiv) in methanol (4 mL) was added alkyl halide (10.0 equiv). The reaction mixture was stirred at room temperature for 16 h. Upon completion, the suspension was washed with ethyl acetate (20 mL) and water (20 mL), then organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting organic residue was purified by flash chromatography column over silica gel (SiO2) to afford the alkylated quinolone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; In methanol; at 20℃; for 16h; | General procedure: To a suspension of 4-quinolones (4. 0 mmol, 1. 0 equiv) and potassium hydroxide (1.5 equiv) in methanol (4 mL) was added alkyl halide (10.0 equiv). The reaction mixture was stirred at room temperature for 16 h. Upon completion, the suspension was washed with ethyl acetate (20 mL) and water (20 mL), then organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 20 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting organic residue was purified by flash chromatography column over silica gel (SiO2) to afford the alkylated quinolone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
>99% | With Dowtherm A; for 0.666667h;Reflux; | 3-Carboxy-4-quinolone (12.06 g, containing residual water) was heated in Dowtherm A(100 mL) at reflux for 40 minutes. After cooling, the reaction mixture was diluted with100 mL hexanes and allowed to sit for 48 hours, followed by vacuum filtration, rinsingwith further hexanes (300 mL) to provide the product as an off-white, powdery solid(9.28 g, >99% from 3-carbethoxy-4-quinolone). |
Tags: 529-37-3 synthesis path| 529-37-3 SDS| 529-37-3 COA| 529-37-3 purity| 529-37-3 application| 529-37-3 NMR| 529-37-3 COA| 529-37-3 structure
[ 23699-65-2 ]
1-(3-(Phenylamino)phenyl)ethanone
Similarity: 0.90
[ 948573-55-5 ]
4-Oxo-1,4-dihydroquinoline-7-carboxylic acid
Similarity: 0.82
[ 1677-44-7 ]
6-Methyl-2,4-dihydroxyquinoline
Similarity: 0.81
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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