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Chemical Structure| 5263-87-6 Chemical Structure| 5263-87-6
Chemical Structure| 5263-87-6

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Synonyms: p-Quinanisole

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Product Details of 6-Methoxyquinoline

CAS No. :5263-87-6
Formula : C10H9NO
M.W : 159.18
SMILES Code : COC1=CC2=C(C=C1)N=CC=C2
Synonyms :
p-Quinanisole
MDL No. :MFCD00006800
InChI Key :HFDLDPJYCIEXJP-UHFFFAOYSA-N
Pubchem ID :14860

Safety of 6-Methoxyquinoline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 6-Methoxyquinoline

* 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.

  • Downstream synthetic route of [ 5263-87-6 ]

[ 5263-87-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 5263-87-6 ]
  • [ 6563-13-9 ]
YieldReaction ConditionsOperation in experiment
97% With dihydrogen peroxide; In water; for 0.25h;Sonication; In a 50 mL round-bottom flask, 1.59 g of 6-methoxyquinoline and then 1.1 g of hydrogen peroxide (35% by mass) were successively added.5% mass fraction of perfluorosulfonic acid resin, 10 ml of water as a solvent, and the resulting mixture in an ultrasonic reaction apparatus at 60 W/The reaction was performed for 15 minutes under 20 KHz ultrasound. The resin catalyst in the reaction system was removed by filtration, and the reaction solvent was removed under reduced pressureWater, finally recrystallized to give 1.69 g of 6-methoxyquinoline nitrous oxide in 97% yield.
90% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 24h; General procedure: To a solution of the corresponding quinoline substrate (5 mmol) in CH2Cl2 (30 mL), m-CPBA (7.5 mmol, 1.5 equiv) was added at 0 C. The reaction mixture was allowed to stir at room temperature for 24 h. Next, saturated aq NaHCO3 solution (100 mL) was added to the reaction mixture. Then, the mixture was extracted with CH2Cl2 (3 × 50 mL) and the organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to obtain the pure quinoline N-oxide (70-90% yield).
82% With dihydrogen peroxide; In acetic acid; at 100℃; for 2h; 6-Methoxy quinoline (15 g, 0.094 mol) was dissolved in acetic acid (97 ml) and treated with hydrogen peroxide (37 ml). The mixture was stirred to 100 C. for 2 hours. After evaporation to dryness 100 ml of water was added to the residue until a precipitate appears. Filtration and washing with water gives a yellow precipitate that is dried under vacuum to yield 13.5 g of the title compound as a light yellow solid (82%). MS (m/e): 176.3 (M+H)+.
55% To a solution of 6- methoxyquinoline (2.00 g, 12.6 mmol) in AcOH (10 mL) was added Η202 (30% in water, 1.9 mL, 18.9 mmol), the mixture was heated to 70 C for 21 hours. The mixture was basified with 2M NaOH to pH 8-9 and extracted with CH2C12 (200 mL), the combined organic layer was washed with brine (50 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by silica gel column (EtOAc / MeOH=10 / 1) to give 6- methoxyquinoline 1-oxide (1.20 g, 55%) as a solid.
55% To a solution of 6- methoxyquinoline (2.00 g, 12.6 mmol) in AcOH (10 mL) was added H202 (30% in water, 1.9 mL, 18.9 mmol), the mixture was heated to 70 C for 21 hours. The mixture was basified with 2M NaOH to pH 8-9 and extracted with CH2C12 (200 mL), the combined organic layer was washed with brine (50 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by silica gel column (EtOAc / MeOH=10 / 1) to give 6- methoxyquinoline 1-oxide (1.20 g, 55%) as a solid.
With dihydrogen peroxide; In acetic acid; at 82℃; for 19h; A solution of 6-methoxyquinoline (11.21 g, 70 [MMOL)] in glacial acetic acid is treated dropwise with 30% hydrogen peroxide (15 mL) and then heated at [82C] for 19 hours. The reaction mixture is cooled, poured onto ice and carefully basified with concentrated ammonium hydroxide. The precipitate is collected, washed with hexane and dried in vacuo to provide the title compound (quantitative yield), which is used as such in the next step. MS [ (+) ES, m/z]: 176.1 [M+H] +
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 12h; General procedure: To a solution of the corresponding N-heterocycles (10.0 mmol) in CH2Cl2 (20 mL), m-chloroperoxybenzoic acid (m-CPBA, 20.0 mmol, 2.0 equiv) was added at 0 C. The reaction mixture was allowed to stir at room temperature for 12 h. Then saturated aqueous NaHCO3 (20 mL) was added. The aqueous was extracted with CH2Cl2 (10 mL x 3) and the combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc/n-hexene or EtOAc/MeOH to afford desired N-oxides.
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: To a solution of 6-methylquinoline (270 µL, 2.0 mmol, 1.0 eq) in dry dichloromethane (4.0 mL), m-chloroperbenzoic acid (690 mg, 4.0 mmol, 2.0 eq) was added at 0 C under argon. The mixture was stirred overnight at room temperature, then diluted with dichloromethane and washed with potassium hydroxide (6 M). The organic layers were dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. A mixture of the residue, molecular sieve (4 Å) and tetrabutylammonium bromide (967 mg, 3.0 mmol, 1.5 eq) in dry dichloromethane (200 mL) was stirred for 10 min at room temperature. p-Toluenesulfonic anhydride (979 mg, 3.0 mmol, 1.5 eq) was added and stirring was continued at room temperature overnight. The reaction mixture was filtered and the solvent was evaporated to dryness under reduced pressure. The crude product was purified by column chromatography (cyclohexane/chloroforme 10:15:11:1) to give 297 mg (1.34 mmol, 67%) of the analytically pure compound. C10H8BrN; MW: 222; 1H NMR (CDCl3, 400 MHz): δ 7.99-7.87 (m, 2H), 7.62-7.53 (m, 2H), 7.46 (d, J = 8.5 Hz, 1H), 2.52 (s, 3H); 13C NMR (CDCl3, 100 MHz): δ 147.3, 140,9, 137.9, 137.3, 132.9, 128.4, 127.1, 126.7, 125.8, 21.7.; MS (ESI): 223 (M+H)+.
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; General procedure: 77% 3-chloroperbenzoic acid (m-CPBA) (3 mmol) in CH2Cl2 (5 mL) was dropped into a solutionof quinoline derivatives (2 mmol) in CH2Cl2 (5 mL) cooled to 0 under vigorous magnetic stirringfor overnight. After the completion of this course, the reaction mixture was allowed up to roomtemperature and stirred overnight. An aqueous solution of saturated NaHCO3 was added to themixture to neutralize residual m-CPBA. The resulting mixture was extracted with CH2Cl2 (3 × 10mL). The organic phase was combined and washed with saturated NaCl solution (3 × 5 mL). The organiclayer was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to givecrude products, which were purified by column chromatography (silica gel 200-300 mesh, AcOEt:MeOH (95:05) as eluent). The products were identified by 1H NMR and MS spectra and comparedto the previous literature.

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  • 3
  • [ 5263-87-6 ]
  • [ 51323-43-4 ]
  • m-N-(boronobenzyl)-6-methoxyquinolinium bromide [ No CAS ]
  • 5
  • [ 5263-87-6 ]
  • cobalt(II) sulphate heptahydrate [ No CAS ]
  • [ 547-32-0 ]
  • Co(sulfadiazine)<SUB>2</SUB>(6-methoxyquinoline)<SUB>2</SUB> [ No CAS ]
 

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