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[ CAS No. 148-24-3 ] {[proInfo.proName]}

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Chemical Structure| 148-24-3
Chemical Structure| 148-24-3
Structure of 148-24-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 148-24-3 ]

CAS No. :148-24-3 MDL No. :MFCD00006807
Formula : C9H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :MCJGNVYPOGVAJF-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :1923
Synonyms :
8-Quinolinol;8-Oxychinolin;NSC 2039;Oxyquinoline;Oxine

Calculated chemistry of [ 148-24-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.77
TPSA : 33.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 2.02
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.76

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.3 mg/ml ; 0.00206 mol/l
Class : Soluble
Log S (Ali) : -2.34
Solubility : 0.659 mg/ml ; 0.00454 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.115 mg/ml ; 0.000791 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 148-24-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P202-P261-P264-P270-P272-P273-P280-P301+P310+P330-P302+P352-P305+P351+P338+P310-P308+P313-P333+P313-P391-P405-P501 UN#:2811
Hazard Statements:H301-H317-H318-H360-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 148-24-3 ]

* 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.

  • Upstream synthesis route of [ 148-24-3 ]
  • Downstream synthetic route of [ 148-24-3 ]

[ 148-24-3 ] Synthesis Path-Upstream   1~79

  • 1
  • [ 148-24-3 ]
  • [ 521-74-4 ]
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YieldReaction ConditionsOperation in experiment
37% With bromine In chloroform at 20℃; for 48 h; Darkness General procedure: To synthesize brominated 8-substituted quinolines (5-10) experimental procedures were repeated in literature [19]. In brief, to a solution of 8-substituted quinoline 2-4 (2 mmol, 1 eq) in distilled CHCl3 (15 mL) was added a solution of molecular bromine (different eqivalents) in CHCl3 over 10 min in the dark at ambient temperature and stirred for 2 days. The reaction was monitored by TLC; after completion of the reaction, the organic layer was washed with 5percent NaHCO3 (3 × 20 mL), dried over Na2SO4, and concentrated under reduced pressure. The products was isolated by alumina column, eluting with AcOEt/hexane (1:5, 150 mL).
Reference: [1] Letters in Drug Design and Discovery, 2017, vol. 14, # 12, p. 1415 - 1424
  • 2
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  • [ 13019-32-4 ]
Reference: [1] Patent: US2005/10048, 2005, A1, . Location in patent: Page/Page column 40 - 41
  • 3
  • [ 148-24-3 ]
  • [ 10218-87-8 ]
  • [ 13019-32-4 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 6, p. 998 - 1006
  • 4
  • [ 148-24-3 ]
  • [ 1198-14-7 ]
  • [ 521-74-4 ]
  • [ 13019-32-4 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 22, p. 4999 - 5004
  • 5
  • [ 148-24-3 ]
  • [ 773-76-2 ]
  • [ 130-16-5 ]
Reference: [1] Chemical Science, 2018, vol. 9, # 7, p. 1782 - 1788
[2] Journal of the Indian Chemical Society, 1945, vol. 22, p. 171
  • 6
  • [ 56-81-5 ]
  • [ 88-75-5 ]
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  • [ 130-16-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1947, p. 969
[2] Roczniki Chemii, 1936, vol. 16, p. 519,522[3] Chem. Zentralbl., 1937, vol. 108, # I, p. 3142
  • 7
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  • [ 130-16-5 ]
Reference: [1] Chemische Berichte, 1919, vol. 52, p. 193
[2] Acta Pharmaceutica Internationalia, 1951, vol. 2, p. 149,154
  • 8
  • [ 110288-09-0 ]
  • [ 580-20-1 ]
  • [ 148-24-3 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 36, p. 4253 - 4256
  • 9
  • [ 91-22-5 ]
  • [ 580-18-7 ]
  • [ 148-24-3 ]
  • [ 118-92-3 ]
  • [ 112259-26-4 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, p. 1722 - 1724
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 9, p. 1065 - 1072
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 9, p. 1065 - 1072
  • 10
  • [ 91-22-5 ]
  • [ 580-18-7 ]
  • [ 148-24-3 ]
  • [ 112259-26-4 ]
  • [ 141977-87-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 9, p. 1065 - 1072
  • 11
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  • [ 580-18-7 ]
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  • [ 118-92-3 ]
  • [ 112259-26-4 ]
  • [ 141977-87-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 9, p. 1065 - 1072
  • 12
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  • [ 578-67-6 ]
  • [ 10470-83-4 ]
  • [ 59-31-4 ]
  • [ 529-37-3 ]
  • [ 529-23-7 ]
Reference: [1] Journal of Physical Chemistry B, 1997, vol. 101, # 14, p. 2650 - 2658
  • 13
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  • [ 394-68-3 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 30, p. 11482 - 11484
[2] Patent: WO2012/142162, 2012, A2, . Location in patent: Page/Page column 24
[3] Organic Letters, 2015, vol. 17, # 3, p. 544 - 547
[4] Journal of the American Chemical Society, 2017, vol. 139, # 4, p. 1452 - 1455
[5] Journal of the American Chemical Society, 2017, vol. 139, # 4, p. 1452 - 1455
  • 14
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  • [ 10470-83-4 ]
YieldReaction ConditionsOperation in experiment
44% With potassium dihydrogenphosphate; Fremy's salt In water; acetone at 20℃; for 3.16667 h; Example 2.1: Procedure for the Preparation of the Starting Materials; Typically a solution of Fremy's salt (1 g, 4 mmol) and potassium dihydrogenphosphate (400 mg, 3 mmol) in water (75 ml) was stirred at room temperature for 10 min then the quinolinol (6 mmol) in acetone (70 ml) was added. The mixture was stirred for 30 min, then a further solution of Fremy's salt (1 g) and potassium dihydrogenphosphate (400 mg) in water (30 ml) was added and the mixture stirred for 30 min, then a further solution of Fremy's salt (1 g) and potassium dihydrogenphosphate (400 mg) in water (30 ml) was added and the mixture stirred for a further 2 h. The mixture was extracted into dichloromethane, dried and evaporated in vacuo to give the product as an orange gum. Purification by column chromatography over silica gel eluting with ethyl acetate (0 - 40percent ) in dichloromethane gave the products as orange solids.The following quinolines were prepared using this method; 5,8-Dihydro-5,8-dioxoquinoline (reg. no. 858471-89-3); 8-Hydroxyquinoline (1 g, 7 mmol) to give quinone (0.48 g, 44percent).
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 7, p. 1439 - 1450
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 15, p. 2731 - 2742
[3] Tetrahedron Letters, 2001, vol. 42, # 26, p. 4329 - 4331
[4] Synthetic Communications, 1999, vol. 29, # 18, p. 3063 - 3066
[5] Patent: WO2006/31134, 2006, A1, . Location in patent: Page/Page column 18-19
[6] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 21, p. 9432 - 9442
[7] Polish Journal of Chemistry, 1998, vol. 72, # 1, p. 122 - 126
[8] Chemische Berichte, 1954, vol. 87, p. 1236,1250
[9] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 1, p. 125 - 130
[10] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1991, vol. 46, # 3, p. 326 - 338
[11] Journal of the Chemical Society, 1953, p. 3161,3166
[12] Tetrahedron Letters, 2013, vol. 54, # 24, p. 3147 - 3149
[13] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4609 - 4620
  • 15
  • [ 75-91-2 ]
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  • [ 75-65-0 ]
Reference: [1] Green Chemistry, 2010, vol. 12, # 6, p. 1076 - 1082
  • 16
  • [ 75-91-2 ]
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  • [ 10470-83-4 ]
  • [ 84288-96-0 ]
  • [ 75-65-0 ]
Reference: [1] Green Chemistry, 2010, vol. 12, # 6, p. 1076 - 1082
  • 17
  • [ 91-22-5 ]
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  • [ 578-67-6 ]
  • [ 10470-83-4 ]
  • [ 59-31-4 ]
  • [ 529-37-3 ]
  • [ 529-23-7 ]
Reference: [1] Journal of Physical Chemistry B, 1997, vol. 101, # 14, p. 2650 - 2658
  • 18
  • [ 148-24-3 ]
  • [ 5541-67-3 ]
Reference: [1] Helvetica Chimica Acta, 1956, vol. 39, p. 1676,1680
  • 19
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  • [ 70125-16-5 ]
Reference: [1] Patent: US2121449, 1936, ,
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 19, p. 4741 - 4749
[3] Patent: US2892841, 1956, ,
  • 20
  • [ 148-24-3 ]
  • [ 15450-76-7 ]
Reference: [1] Monatshefte fuer Chemie, 1895, vol. 16, p. 761
[2] Chemistry and Industry (London, United Kingdom), 1957, p. 1271
  • 21
  • [ 148-24-3 ]
  • [ 6640-50-2 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogen In water at 20℃; for 0.666667 h; The 100mmol 8-hydroxy quinoline and load 0.7mmol catalyst polymer microspheres [...] Poly (DVB-co-NVP) Rh and 500 ml of water are added in a reaction kettle, to hydrogen replaces the cauldron five times the air in, and then filled with hydrogen, the reaction at normal temperature and pressure 40 minutes, the aqueous phase is extracted three times with ethyl ether, the merger ether level, ethyl ether evaporate after drying, to obtain 8-hydroxy -1, 2, 3, 4-tetrahydro-quinoline, yield 95percent.
93% With sodium tetrahydroborate In ethanol; water at 60℃; for 3 h; Inert atmosphere Precatalyst (50 mg), NaBH4 (or NaBD4) (3e12 mmol), 1 mmol ofthe N-cyclic substrate and 5 ml deionized and degassed water (orD2O) were placed in a 25 ml three-necked flask equipped with areflux condenser and a pressure release valve to discharge thehydrogen gas self-generated during the reactions. The operationwas carried out under inert atmosphere. The reaction mixture wasvigorously stirred at different temperatures (25e60 C) for the timeselected. The complete conversion of substrate was determined bysubmitting small samples to spot thin layer chromatography (TLC).After completion, the slurry was centrifuged to separate the catalyst.The solid phase obtained was washed with deionized H2O andthen several times with ethyl acetate to remove all organic residue.The filtrate was collected, extracted with ethyl acetate and theextract dried over anhydrous MgSO4. After removal of the solvent invacuo, the corresponding product was obtained. In some cases, asilica-gel column chromatography was used to purify the product(isolated yield). The product analysis and identification was conductedby comparing the NMR spectral data with those of thepublished pure substances (all analyzed by 1H NMR and 13C NMRon Bruker Avance II 400 MHz spectrometer). The reaction selectivitieswere obtained from the NMR spectra by integration ofcharacteristic peaks for the product and reactant.
91%
Stage #1: With H2SiEt2; tris(pentafluorophenyl)borate In chloroform at 85℃; for 2 h; Inert atmosphere
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1 h;
General procedure: In a 1.5 mL reaction vial, B(C6F5)3 (0.025 mmol, 5.0 mol percent) was dissolved in chloroform (0.60 mL), towhich diethylsilane (1.75 mmol, 3.5 equiv) was added. After shaking briefly, quinolines (1a-p, 0.50 mmol, 1.0equiv) was subsequently added to the above catalyst solution under argon atmosphere. The reaction mixturewas stirred at 25-65 oC for 6-24 h for the reaction of 1a-h, and at 25-100 oC for 2-24 h for the reaction of 1i-p,then allowed to cool down to room temperature and concentrated under reduced pressure to give the crudeproduct. This reaction mixture was then treated with 0.25 N HCl ethereal solution (7 mL) and stirred at roomtemperature for 1 h to give the solid residue, which was subsequently washed with ether. The solid residue wasthen dissolved or suspended in MeOH (1.0 mL) and neutralized with Na2CO3·H2O (0.5 g) at 0 oC. After stirringfor 2 h, MeOH was removed under reduced pressure, and the neutralized reaction residue was dissolved inCH2Cl2 and washed with brine (5 mL) and water (5 mL). The crude product was then obtained from the organicphase of CH2Cl2 solution and finally purified by column chromatography on silica gel to give 2a-h(EtOAc/Hexane = 1/9) and 2i-p (EtOAc/Hexane = 3/7).
Reference: [1] Chemical Communications, 2013, vol. 49, # 63, p. 7052 - 7054
[2] Patent: CN105884684, 2016, A, . Location in patent: Paragraph 0018; 0019
[3] Journal of Organic Chemistry, 2008, vol. 73, # 21, p. 8639 - 8642
[4] Tetrahedron, 2009, vol. 65, # 47, p. 9737 - 9741
[5] Journal of Organometallic Chemistry, 2016, vol. 821, p. 197 - 205
[6] Chemistry - A European Journal, 2016, vol. 22, # 48, p. 17151 - 17155
[7] Synlett, 2017, vol. 28, # 18, p. 2396 - 2400
[8] ACS Catalysis, 2016, vol. 6, # 9, p. 5816 - 5822
[9] Advanced Synthesis and Catalysis, 2016, vol. 358, # 19, p. 3039 - 3045
[10] Advanced Synthesis and Catalysis, 2015, vol. 357, # 4, p. 753 - 760
[11] Organic Letters, 2018, vol. 20, # 14, p. 4159 - 4163
[12] Angewandte Chemie - International Edition, 2016, vol. 55, # 1, p. 292 - 296[13] Angew. Chem., 2016,
[14] Chemical Science, 2018, vol. 9, # 42, p. 8134 - 8141
[15] Synthetic Communications, 1998, vol. 28, # 3, p. 485 - 492
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[17] Chemische Berichte, 1881, vol. 14, p. 1368
[18] Journal of the American Chemical Society, 1944, vol. 66, p. 1166,1168
[19] Helvetica Chimica Acta, 1949, vol. 32, p. 1278,1281
[20] Helvetica Chimica Acta, 1949, vol. 32, p. 1278,1281
[21] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1933 - 1939
[22] Patent: US4843082, 1989, A,
[23] Synthesis, 2011, # 13, p. 2079 - 2084
[24] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17592 - 17598,7
[25] RSC Advances, 2013, vol. 3, # 46, p. 23984 - 23988
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[27] Journal of the American Chemical Society, 2017, vol. 139, # 28, p. 9419 - 9422
[28] Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14167 - 14172
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[30] Catalysis Science and Technology, 2018, vol. 8, # 19, p. 5019 - 5097
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  • [ 32258-81-4 ]
  • [ 6640-50-2 ]
Reference: [1] Synlett, 2004, # 15, p. 2827 - 2829
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  • [ 7664-93-9 ]
  • [ 7732-18-5 ]
  • [ 6640-50-2 ]
Reference: [1] Helvetica Chimica Acta, 1949, vol. 32, p. 1278,1281
  • 24
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  • [ 1127-45-3 ]
YieldReaction ConditionsOperation 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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[3] Journal of the Chemical Society, 1954, p. 570,572
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  • 30
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YieldReaction ConditionsOperation in experiment
115 mg
Stage #1: With sodium hydroxide In ethanol; water
Stage #2: With water In ethanol for 20 h; Reflux
Stage #3: With hydrogenchloride In water
8-Hydroxyquinoline (5 g, 0.3 mol) was dissolved in ethanol (50 mL) to which was added sodium hydroxide (10 g, 0.25 mol) dissolved in water (15 mL). The solution was refluxed during which time chloroform was added dropwise over 30 min. After refluxing for 20 h, ethanol and excess chloroform were evaporated in vacuo. The resulting residue was dissolved in 150 mL of water and the solution was made slightly acidic by adding dilute hydrochloric acid. The resulting yellow colored solid was extract with dichloromethane then purified by column chromatography (silica gel, dichloromethane/methanol) to afford the title product as a white solid (115 mg, 0.67 mmol). 1H-NMR (CDCl3-400 MHz) d = 10.16 (s, 1H), 9.71 (dd, 1H, J = 1.6Hz, 8.4Hz), 8.89 (dd, 1H, J = 1.6Hz, 4.0Hz), 8.02 (d, 1H, J = 8.0Hz), 7.69 (q, 1H, J = 4.0Hz), 7.30 (d, 1H, J = 8.0Hz); 13C-NMR (DMSO-d6-400 MHz) d = 193.1, 160.5, 149.9, 141.1, 138.9, 133.9, 127.7, 125.5, 123.4, 111.7.
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[10] Nippon Kagaku Zasshi, 1956, vol. 77, p. 1107[11] Chem.Abstr., 1959, p. 5267
[12] Helvetica Chimica Acta, 1956, vol. 39, p. 1676,1680
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[2] Journal of the American Chemical Society, 1955, vol. 77, p. 6671,6672
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 6671,6672
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[3] Nippon Kagaku Zasshi, 1956, vol. 77, p. 1107[4] Chem.Abstr., 1959, p. 5267
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[2] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 44, p. 439,442
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[3] Chemische Berichte, 1916, vol. 49, p. 16
[4] Journal of the American Chemical Society, 1935, vol. 57, p. 124,127
  • 38
  • [ 148-24-3 ]
  • [ 6541-19-1 ]
YieldReaction ConditionsOperation in experiment
29% With hydrogenchloride; sodium chlorate In water for 2 h; Sodium chlorate (0.50 mol) was added over a period of 1 h to a solution of 8-hydroxyquinoline (0.10 mol) in concd HCl (600 mL) at 40 °C and the reaction mixture stirred for 2 h before being diluted with water to a total volume of 2 L.
The white precipitate that formed was removed by filtration and discarded.
The filtrate was then extracted with CH2Cl2 (6 * 250 mL), the organic phases were combined, washed with water and concentrated in vacuo to give a yellow solid.
The solid was then recrystallized in MeOH to yield 7 as bright yellow crystals.
The characterization data for compound 7 are in accordance with that reported previously [
32
].
12% With hydrogenchloride; calcium chlorate In water Example 1; Quinoline Phthalocyanine; a) 6,7-dicyano-5,8-dihydroxyquinoline 3; 6,7-Dichloro-5,8-quinolinedione 2 was prepared in low yield from commercially available 8-hydroxyquinoline 1 by modification of a literature procedure (Shaikh, I. A.; Johnson, F.; Grollman, A. P. J. Med. Chem. 1986, 29, 1329). A solution of potassium cyanide (1.02 g; 16 mmol) in water (3 mL) was added to a boiling solution of the dichloroquinone 2 (794 mg; 3.48 mmol) in THF/methanol (1:1, 40 mL) and heating was continued for a further 2 min. The reaction mixture was concentrated to half-volume and diluted to the original volume with water. Hydrochloric acid (10 M) was added cautiously [Caution: HCN fumes] causing the reaction mixture to change from an olive-green solution to a pale brown suspension. The solid was filtered off, washed with water and air dried overnight thereby affording the dinitrile 3 as a chocolate-brown solid (509 mg, 69percent).
Reference: [1] RSC Advances, 2015, vol. 5, # 78, p. 63330 - 63337
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 8, p. 4617 - 4625
[3] Journal of Medicinal Chemistry, 1986, vol. 29, # 8, p. 1329 - 1340
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 9, p. 3238 - 3251
[5] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 423 - 436
[6] Patent: US2006/30701, 2006, A1, . Location in patent: Page/Page column 25-26
[7] Chemistry of Heterocyclic Compounds, 2012, vol. 48, # 6, p. 888 - 891[8] Khim. Geterotsikl. Soedin., 2012, vol. 48, # 6, p. 955 - 959,5
[9] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1572 - 1577
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Reference: [1] Chemical Science, 2018, vol. 9, # 7, p. 1782 - 1788
[2] Journal of the Indian Chemical Society, 1945, vol. 22, p. 171
  • 45
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Reference: [1] Chemische Berichte, 1888, vol. 21, p. 2979,2983
[2] Chemische Berichte, 1897, vol. 30, p. 2420[3] Journal fuer Praktische Chemie (Leipzig), 1897, vol. <2> 56, p. 282
[4] Chemische Berichte, 1919, vol. 52, p. 193
[5] Chemische Berichte, 1897, vol. 30, p. 2420[6] Journal fuer Praktische Chemie (Leipzig), 1897, vol. <2> 56, p. 282
[7] Chemische Berichte, 1888, vol. 21, p. 2979,2983
[8] RSC Advances, 2015, vol. 5, # 107, p. 88311 - 88315
[9] DRP/DRBP Org.Chem.,
  • 46
  • [ 148-24-3 ]
  • [ 83-73-8 ]
YieldReaction ConditionsOperation in experiment
87% at 80℃; for 1 h; Inert atmosphere 8-Hydroxyquinoline (0.1 g, 0.69 mmol) and l-butyl-3-methylpyridinium dichloroiodate (BMPDCI) (0.31 g, 0.89 mmol) were added in 10 ml of one neck round bottomed flask in an inert atmosphere and then heated at 80 °C for lhr. After the reaction was completed (TLC), ethyl acetate (10ml) was added followed by addition of water (10ml). The entire reaction mixture was extracted with ethyl acetate (3x10ml). The combined organic layers were dried using sodium sulphate and concentrated on rotavapor to afford the crude product. This was further purified by silica gel column chromatography to afford 0.24 g (87 percent) of pure 5,7- diiodo-8-hydroxyquinoline as a solid. (M.P. decomposes >210 °C) 1H NMR (DMSO-d6 δ/ppm): 8.88 (d, 1H, 7=4 Hz, Ar-H), 8.3 (s, 1H, Ar-H), 8.27-8.31 (dd, 1H, 7=1.3 Hz, 8.6 Hz, Ar-H), 7.75 (q, 1H, 7=4.2 Hz, 8.6 Hz, Ar-H).
82% With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite In water; acetic acid at 25℃; for 3 h; General procedure: Iodination of phenol (1d) in the presence of Na2SO3 (typical procedure). A 100-mL round-bottom flask was charged with a solution of 3 mmol of phenol in 10 mL of acetic acid, and a solution of KI3 and Na2SO3 (prepared preliminarily by addition of 3 mmol of iodine and 3 mmol of Na2SO3 to a solution of 3 mmol of potassium iodide in 3 mL of water) was added rapidly. At the same time, a solution of 3 mmol of NaIO4 in 5 mL of water was added, and 0.5 mL of sulfuric acid was rapidly added using a pressure-equalizing dropping funnel. The mixture was stirred at 25°C, the progress of the reaction being monitored by TLC. When the reaction was complete, the mixture was poured into ice-cold water, and the solid product was separated by vacuum filtration, washed twice with deionized water, and dried.
Reference: [1] Tetrahedron, 2008, vol. 64, # 1, p. 234 - 239
[2] Tetrahedron Letters, 2001, vol. 42, # 11, p. 2089 - 2092
[3] Patent: WO2016/113757, 2016, A1, . Location in patent: Page/Page column 18-19
[4] Molecules, 2005, vol. 10, # 10, p. 1307 - 1317
[5] Monatshefte fur Chemie, 2012, vol. 143, # 4, p. 619 - 623
[6] Russian Journal of Organic Chemistry, 2016, vol. 52, # 3, p. 433 - 436[7] Zh. Org. Khim., 2016, vol. 52, # 3, p. 433 - 436,4
[8] Afinidad, 1951, vol. 28, p. 163,166
[9] Chemische Berichte, 1952, vol. 85, p. 104,106
[10] Trudy Inst. c. chim. Reakt., 1939, vol. 16, p. 80,82[11] Chem.Abstr., 1940, p. 2745
[12] Journal fuer Praktische Chemie (Leipzig), 1936, vol. <2> 145, p. 257,261
[13] Journal of the American Chemical Society, 1936, vol. 58, p. 1314
[14] Bulletin de la Societe Chimique de France, 1954, p. 226
[15] Journal of Organic Chemistry, 1957, vol. 22, p. 1111
[16] Journal of Fluorescence, 2018, vol. 28, # 5, p. 1121 - 1126
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1936, vol. <2> 145, p. 257,261
[2] Journal of the Indian Chemical Society, 1944, vol. 21, p. 354,356
[3] Trans. elektroch. Soc., 1939, vol. 75, p. 385
  • 48
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Reference: [1] Journal of Organic Chemistry, 1957, vol. 22, p. 1111
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Reference: [1] ACS Chemical Neuroscience, 2014, vol. 5, # 10, p. 952 - 962
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997, vol. 36, # 11, p. 1071 - 1073
[3] Chemistry of Heterocyclic Compounds, 2005, vol. 41, # 8, p. 1027 - 1030
[4] Russian Journal of Organic Chemistry, 2004, vol. 40, # 1, p. 93 - 96
[5] Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 45, p. 540
[6] Molecules, 2010, vol. 15, # 1, p. 288 - 304
[7] Archives of Pharmacal Research, 2013, vol. 36, # 1, p. 32 - 40
[8] Dalton Transactions, 2015, vol. 44, # 48, p. 20913 - 20925
[9] RSC Advances, 2016, vol. 6, # 9, p. 7139 - 7158
[10] Asian Journal of Chemistry, 2017, vol. 29, # 4, p. 742 - 748
[11] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1572 - 1577
[12] Medicinal Chemistry Research, 2018, vol. 27, # 4, p. 1093 - 1102
[13] Journal of Fluorescence, 2018, vol. 28, # 5, p. 1121 - 1126
  • 50
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Reference: [1] Inorganica Chimica Acta, 2003, vol. 342, p. 97 - 106
  • 51
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  • [ 620-24-6 ]
  • [ 13826-35-2 ]
YieldReaction ConditionsOperation in experiment
93% With sodium chloride; sulfuric acid; sodium hydrogencarbonate; potassium carbonate In chlorobenzene EXAMPLE 1
m-Hydroxybenzyl alcohol (50.0 g; 0.40 mole), 90.0 g (0.80 mole) of chlorobenzene, 156.6 g (1.37 moles) of N,N'-dimethylimidazolidinone and 41.8 g (0.30 mole) of potassium carbonate were mixed, and 0.8 g of cuprous chloride and 1.2 g of 8-hydroxyquinoline were added.
The mixture was heated to 150oC in an inert gaseous atmosphere.
The mixture was stirred for 17 hours while continuing refluxing and dehydration.
During this time, the reaction temperature gradually rose and reached 162oC at the end of 17 hours.
The mixture was further heated to 170oC, and stirred for 3 hours at this temperature.
After the reaction, the reaction mixture was cooled and 200 ml of 5percent cold dilute sulfuric acid was added.
The mixture was extracted with ether, and the ethereal layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. GLC analysis showed that the conversion of m-hydroxybenzyl alcohol was 100 percent, the selectivity of m-phenoxybenzyl alcohol was 93 percent, and the yield of m-phenoxybenzyl alcohol was 93 percent.
Reference: [1] Patent: EP202838, 1991, B1,
[2] Patent: US4694110, 1987, A,
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  • 59
  • [ 148-24-3 ]
  • [ 50-00-0 ]
  • [ 4053-45-6 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In water at 0 - 20℃; for 8 h; A mixture of 14.6 g (0.1 mol) of 8-quinolinol, 16 mL of 32percent HC1 in water, and 16 mL (0.1 mL) of 37percent formaldehyde in water at 0 °C was treated with hydrogen chloride gas for 6 h. The solution was allowed to stand at room temperature for 2 h without stirring. The yellow solid obtained was collected on a filter, washed with 90percent alcohol and dried under vacuum to give 5-chloromethyl-8-quinolinol hydrochloride A (19.0 g, 98percent): 1H NMR (250 MHz, CDC13, 5) 5.32 (s, 2H), 7.53 (m, 1H), 7.85 (m, 2H), 8.12 (m, 1H), 9.12 (m, 1H), 9.28 (m, 1H).
98% With hydrogenchloride In water at 20℃; for 6 h; Thus, a mixture of 10.0 g (0.068 mol) of 8-hydroxyquinoline, 11 ml of concentrated hydrochloric acid, and 11 ml (0.397 mol) of 37percent formaldehyde was treated with hydrogen chloride gas and stirred for 6 h.
The solution was allowed to stand at room temperature for 2 h without stirring.
The obtained yellow solid was collected on a filter, washed with acetone, and dried under vacuum to afford 5-chloromethyl-8-hydroxyquinoline hydrochloride (Cl-QH) (9.8 g, 98percent) without further purification, m.p.: 282 °C, Rf Value: 0.52 (n-hexane/acetone: 4/6). The 1HNMR, 13C NMR, IR and mass spectroscopy (ESI-MS) (Table 1)were used to characterize and confirm the obtained product structure
78% With hydrogenchloride; zinc(II) chloride In water for 12 h; A mixture of 5.84 g (40.0 mmol) of 8-quinolinol, 50 ml of concentrated hydrochloric acid, and 6.4 ml of 37percent formaldehyde was treated with 0.6 g of zinc chloride and stirred for 12 h. The mixture was filtered,washed with copious acetone and dried to give compound 2 as a yellow solid (7.2g, 78percent). 1H NMR (400 MHz, Deuterium Oxide) δ 9.12 (dd, J = 8.7, 1.4 Hz, 1H), 8.88 (dd, J = 5.5, 1.4 Hz, 1H), 7.97 (dd, J = 8.7, 5.4 Hz, 1H), 7.59 (d, J = 8.0 Hz, 1H), 7.24 (d, J = 7.9 Hz, 1H), 4.93 (s, 2H).
78% With hydrogenchloride In water at 20℃; for 8 h; Cooling with ice To a 100 mL round bottom flask was added 14. 50 g (100 mmol) of 8-hydroxyquinoline,16 mL concentrated hydrochloric acid,16 mL of 37percent formaldehyde solution,Hydrogen chloride gas was bubbled under ice bath for 6h,Stirring at room temperature for 2h,Filtration,Washed,Vacuum drying,To give a yellow solid15. 12 g,Yield 78percent.
77.5% With hydrogenchloride In water at 0 - 20℃; for 10 h; To a cooled solution of comercial 8-hydroxyquinoline (14.6 g, 100 mmol) in conc. HCl (44 mL) at 0 °C, a 37percent aqueous formaldehyde solution (20 mL) was added.
Then HCl gas was bubbled through the solution with stirring for 2 h.
The mixture was allowed to warm to rt with further stirring for 6 h and without stirring for 2 h more.
The product was filtered and the solid was rinsed with conc. HCl, giving product 9 (19.9 g, 77.5percent) as light yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 5.30 (s, 2H), 7.51 (d, J= 8.0 Hz, 1H), 7.86 (d, J= 8.0 Hz, 1H), 8.13 (dd, J= 8.7, 5.2 Hz, 1H), 9.12 (dd, J= 5.1, 1.3 Hz, 1H), 9.24 (dd, J= 8.8, 1.3 Hz, 1H).
69% With hydrogenchloride In water at 50℃; for 8 h; CHQ was synthesized according to the literature [28]. Briefly, a stream of HCl gas was bubbled into the solutionof 8-hydroxyquinoline (1.45 g, 10 mmol) in concentrated HCl (5 mL) and aqueous solution of formaldehyde 37percent(2 mL) under stirring at 50°C for 8 h. The reaction mixture was then filtered and the residual solid was washed with concentrated HCl (4 × 5 mL) and dried under vacuum.Compound was obtained as a yellow solid (1.3 g,69percent). FTIR (KBr): ν 2100–3100 (O―H), 2835 (CH2),1547, 1597 (C=C), 1497 (CH2)OOP, 1200–1300 (C―O),785, 725 (C―Cl) cm−1.
68% With hydrogenchloride In water at 25℃; for 6 h; Hydrochloric acid at 37percent (10 ml) is added, dropwise, with vigorous stirring, to a suspension of 8-hydroxyquinoline (2.9 g; 20 mmol) in formaldehyde (4 ml). The medium becomes homogeneous and bright yellow and heat is strongly given off during the addition. Hydrochloric acid gas is bubbled through the medium for 1 h and then the stirring is continued for 5 h. The temperature gradually decreases to approximately 25° C. and a fine yellow precipitate appears. The medium is then filtered and the residual yellow solid is washed with hydrochloric acid at 37percent (4×5 ml), and then dried under a high vacuum. Compound 7 is obtained in the form of a bright yellow hygroscopic solid (3.15 g; 13.7 mmol; 68percent) immediately stored under argon at 4° C. 1H NMR (DMSO-d6, 300 MHz) δ (ppm): 9.24 (dd, 4J=1.2 Hz, 3J=8.7 Hz, 1H); 9.13 (dd, 4J=1.2 Hz, 3J=5.2 Hz, 1H); 8.13 (dd, 3J=5.2 Hz, 3J=8.7 Hz, 1H); 7.87 (d, 3J=8.1 Hz, 1H); 7.54 (d, 3J=8.1 Hz, 1H); 5.32 (s, 2H). 13C NMR (DMSO-d6, 75 MHz) δ (ppm): 149.5; 144.4; 142.9; 132.3; 129.6; 127.8; 124.6; 122.8; 115.2; 43.1.

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