* 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.
Reference：
[1] Journal of Chemical Sciences, 2010, vol. 122, # 6, p. 847 - 855
[2] Organic Process Research and Development, 2004, vol. 8, # 4, p. 663 - 665
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 19, p. 4741 - 4749
2
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[ 15450-76-7 ]
Reference：
[1] Canadian Journal of Chemistry, 2005, vol. 83, # 5, p. 460 - 470
[2] Journal of Fluorescence, 2018, vol. 28, # 5, p. 1121 - 1126
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[ 148-24-3 ]
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Yield
Reaction Conditions
Operation in experiment
97%
With manganese dioxide; dihydrogen peroxide In dichloromethane
(1) 8-Hydroxyquinoline N-oxide 59.74 g (411 mmol) of 8-hydroxyquinoline, 350 ml (822 mmol) of dichloromethane, 82.2 ml of 35percent aqueous hydrogen peroxide solution and 0.52 g (2.5 mmol) of methylrhenium trioxide (MTO) are placed in a 1 L round-bottomed flask. The reaction mixture is stirred at room temperature (25° C.) for 24 hours, followed by successive addition of 80 ml of aqueous hydrogen peroxide solution and 0.32 g of manganese dioxide. The mixture is stirred for 1 hour 30 minutes and the phases are then separated by settling. The aqueous phase is extracted with dichloromethane (2*200 ml). The organic phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum to give 64 g of 8-hydroxyquinoline N-oxide in the form of an orange-colored solid; m.p.=112° C. (Yield: 97percent)
97%
With manganese dioxide; dihydrogen peroxide In dichloromethane
(1) 8-Hydroxyquinoline N-Oxide 59.74 g (411 mmol) of 8-hydroxyquinoline, 350 ml (822 mmol) of dichloromethane, 82.2 ml of 35percent aqueous hydrogen peroxide solution and 0.52 g (2.5 mmol) of methylrhenium trioxide (MTO) are placed in a 1 l round-bottomed flask. The reaction mixture is stirred at ambient temperature (25° C.) for 24 h and then 80 ml of aqueous hydrogen peroxide solution and 0.32 g of manganese dioxide are successively added. The mixture is stirred for 1 h 30 and then separated by settling. The aqueous phase is extracted with dichloromethane (2*200 ml). The organic phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum to provide 64 g of 8-hydroxyquinoline N-oxide in the form of an organe-colored solid; M.p.=112° C. (Yield: 97percent)
95%
With dihydrogen peroxide; bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt In ethanol at 20℃; for 0.833333 h;
General procedure: In a 25-mL flask to a solution of Hendrickson reagent (1 mmol, 0.839 g) in 3 mL of ethanol at room temperature, H2O2 (4 mmol, 0.4 mL) was added, and the mixture allowed stirring for 15 min. Then, pyridine (1 mmol, 0.16 mL) was added to the mixture, and the solution was stirred again for appropriate time (Table 2). Upon completion of the reaction, the solvent was removed under reduced pressure, and then the saturated sodium bicarbonate solution (10 mL) was added. The product was extracted with chloroform (3 × 5 mL), washed with water, and dried over anhydrous MgSO4. The filtrate was evaporated and the crude product was purified by silica gel column chromatography using ethyl acetate/n-hexane (3:7) as eluent to afford pyridine-N-oxide (0.076 g, 80percent).
89%
With dihydrogen peroxide In water for 0.416667 h; Sonication
In a 50 mL round-bottomed flask, 1.45 g of 8-hydroxyquinoline, followed by hydrogen peroxide (35percent by mass), 1.1 g, 5percent were added.Mass fraction of perfluorosulfonic acid resin, 10 ml of water as a solvent, and the resulting mixture at 30 W/20 KHz in an ultrasonic reactor25 minutes under acoustic conditions. The perfluorosulfonic acid resin catalyst in the reaction system is removed by filtration, and the reaction solvent is removed under reduced pressureThe water was finally recrystallized to obtain a 1.63 g 6-chloroquinoline nitrogen oxide compound in 89percent yield.
76%
With peracetic acid; acetic acid In dichloromethane; water at 0 - 20℃; for 5 h;
To a solution of 8-hydroxyquinoline (50.0 g, 344 mmol) in methylene chloride (325 mL) was added dropwise at 0° C. dilute peroxyacetic acid (Fluka, 39percent in aqueous acetic acid, 75.1 mL, 440 mol), wherein the yellow solution became deep red. After warming and stirring at room temperature for 5 h, a solution of sodium disulfite (14.0 g, 74 mmol) in water (20 mL) was added dropwise. Here the solution turned dark yellow to black. The organic phase was washed successively with 1M hydrochloric acid (ca. 300 mL), sat. sodium hydrogen carbonate solution (ca. 200 mL), sat. potassium carbonate solution (ca. 150 mL) and sat. sodium chloride solution (ca. 200 mL). The yellow-brown solution was treated with silica gel (silica gel 60 for column chromatography, 0.063-0.200 mm, 5 g) and dried with sodium sulfate. After stirring at room temperature for 15 min, the solid was separated off and the solvent was removed on a rotary evaporator. A yellow to light-brownish solid was obtained, which was dried under fine vacuum. [0094] Yield: 42.4 g (263 mmol, 76percent), yellow solid. [0095] HR-ESI/MS (CH3OH): m/z calculated for [C9H7NO2+H]+: 162.0550. found: 162.0553; m/z calculated for [C9H7NO2+Na]+: 184.0374. found: 184.0374. [0096] 1H-NMR (300.1 MHz, CDCl3): δ (ppm)=7.09 (dd, J=7.9, 1.1 Hz, 1H, H7), 7.24-7.29 (m, 2H, H3/H5), 7.51 (t, J=7.9 Hz, 1H, H6), 7.81 (dd, J=8.5, 0.6 Hz, 1H, H4), 8.26 (dd, J=6.1, 1.0 Hz, 1H, H2), 15.09 (s, 1H, OH). [0097] 13C{1H}-NMR (75.5 MHz, CDCl3): δ (ppm)=114.6 (C7), 116.6 (C5), 120.3 (C3), 129.4 (C4), 129.7 (C4a), 130.3 (C6), 132.1 (C8a), 134.3 (C2), 153.8 (C8). [0098] CHN analysis: calculated for C9H7NO2 (161.16 g/mol): C, 67.07; H, 4.38; N, 8.69 wt percent. found: C, 67.14; H, 4.19; N, 8.63 wt percent.
76%
With peracetic acid In dichloromethane; water at 0 - 20℃; for 5.25 h;
To a solution of 8-hydroxyquinoline (50.0 g, 344 mmol) in methylene chloride (325 mL) were diluted peroxyacetic acid (Fluka, ~ 39percent in aqueous acetic acid, 75.1 mL, 440 mol) was added dropwise at 0 ° C, the yellow solution turned deep red.After heating and stirring at room temperature for 5 h, a solution of sodium (14.0 g, 74 mmol) in water (20 mL) was added dropwise.In this case, the solution turned dark yellow to black.The organic phase was washed successively with 1 M hydrochloric acid (300 mL), sat.Sodium bicarbonate solution (200 mL), sat.Potassium carbonate solution (150 mL) and sat.Sodium chloride solution.(Ca. 200 mL).The yellow-brown solution was treated with silica gel (silica gel 60 for column chromatography, 0.063-0.200 mm, 5g) and drying with sodium sulfate.After stirring at room temperature for 15 min, the solid was separated and the solvent removed on a rotary evaporator.This gave a yellow to light tan solid which was dried under vacuum fine. Yield: 42.4 g (263 mmol, 76percent), yellow solid.
70.3%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Cooling with ice
0.5 g 8-hydroxyquinolinewas dissolved in 4 mL dichloromethane and 0.69 g metachloroperbenzoicacid (m-CPBA) was added stepwise in anice-cooled water bath. The resulting mixture was stirred atroom temperature overnight. 7.14 mL 2 M NaOH wasadded slowly to the above solution. The organic layer wasseparated and the water phase was washed with dichloromethane.The organic fractions were combined andwashed with brine, dried with sodium sulfate, and thenfiltered. The organic solvent was removed under reducedpressure, resulting in 0.39 g title compound as yellow solid(yield, 70.3 percent) 1H NMR (300 MHz, CDCl3) d 8.25 (dd,J = 6.0, 0.8 Hz, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.50 (t,J = 8.0 Hz, 1H), 7.25–7.21 (m, 2H), 7.08 (dd, 1H).
40%
at 70℃; for 16 h;
A solution of quinolin-8-ol (4 g, 27.6 mmol) in 35percent hydrogen peroxide solution (10 ml) in acetic acid (25 mL) was stirred at 70 °C for 16 hours. After the reaction mixture was neutralized to pH 12 with ammonium hydroxide, it was extracted with ethyl acetate (50 mL x 3). The organic layers were combined, dried over sodium sulfate and concentrated to dryness to afford 5-2 (1.8 g, 40percent yield) as a brown solid. MS (ESI): m/z 238 [M+H]+.
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[ 79-21-0 ]
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[ 2311-91-3 ]
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[ 93-59-4 ]
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[ 1127-45-3 ]
[ 31568-91-9 ]
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[1] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 5, p. 460 - 470
[3] Journal of Fluorescence, 2018, vol. 28, # 5, p. 1121 - 1126
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[ 1127-45-3 ]
[ 93609-84-8 ]
Reference：
[1] Patent: US2012/46467, 2012, A1,
11
[ 1127-45-3 ]
[ 343788-51-2 ]
Reference：
[1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5576 - 5585
A solution of quinolin-8-ol-N-oxide (5-2) (322 mg, 2 mmol) in acetic anhydride (4 mL) was stirred at 140 °C for 5 hours and then cooled to room temperature. Acetic anhydride was removed under reduced pressure. The residue was neutralized to pH 7 with saturated sodium bicarbonate solution, then extracted with ethyl acetate (20 mL x 3). The organic layers were combined, dried over sodium sulfate and concentrated to dryness to give a tan oil, which was treated with ethanol to provide compound 5-3 (138 mg, 34percent yield) as a brown solid. MS (ESI): m/z 204 [M+H]+.
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