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[ CAS No. 611-36-9 ] {[proInfo.proName]}

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Chemical Structure| 611-36-9
Chemical Structure| 611-36-9
Structure of 611-36-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 611-36-9 ]

CAS No. :611-36-9 MDL No. :MFCD00006777
Formula : C9H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :PMZDQRJGMBOQBF-UHFFFAOYSA-N
M.W :145.16 Pubchem ID :69141
Synonyms :
4-Quinolinol

Calculated chemistry of [ 611-36-9 ]

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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 0.58
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.78
Solubility : 2.42 mg/ml ; 0.0167 mol/l
Class : Very soluble
Log S (Ali) : -0.85
Solubility : 20.6 mg/ml ; 0.142 mol/l
Class : Very 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 : 1.06

Safety of [ 611-36-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 611-36-9 ]

* 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 [ 611-36-9 ]
  • Downstream synthetic route of [ 611-36-9 ]

[ 611-36-9 ] Synthesis Path-Upstream   1~29

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Reference: [1] Patent: US2013/210844, 2013, A1,
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  • [ 3964-04-3 ]
YieldReaction ConditionsOperation in experiment
88% With phosphorus tribromide In N,N-dimethyl-formamide for 0.666667 h; Inert atmosphere Step 1 : To a stirred solution of quinolin-4-ol (4.00 g, 27.6 mmol) in dry DMF (30 mL) was added phosphorus tribromide (7.61 g, 28.2 mmol) dropwise for 10 min. The reddish colored suspension was stirred for 30 min under nitrogen atmosphere. After complete consumption of starting material, the reaction mixture was quenched with ice, stirred for anther 30 min, then basified to pH -10 with a solution of saturated sodium bicarbonate (20 mL). The reaction mixture was extracted with ethyl acetate (2 x 100 mL) and the combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified on silica gel column using dichloromethane / methanol (0percent to 10percent) as eluent to give 4-bromo- quinoline (5.04 g; 88percent) as a yellow solid; LCMS (ESI) 208 (M+H); H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.69 (d, J=4.69 Hz, 1 H), 8.20 (dd, J=8 39, 0.88 Hz, 1 H), 8.08 - 8.16 (m, 1 H), 7.78 (ddd, J=8.39, 6.98, 1 .37 Hz, 1 H), 7.71 (d, J=4.69 Hz, 1 H), 7.66 (ddd, J=8.31 , 7.04, 1.15 Hz, 1 H).
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 12, p. 5652 - 5661
[2] Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 2232 - 2235
[3] Patent: WO2014/121883, 2014, A1, . Location in patent: Page/Page column 51
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 37, p. 9311 - 9316[5] Angew. Chem., 2012, vol. 124, # 37, p. 9445 - 9450,6
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Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2413,2414
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Reference: [1] Journal of the Chemical Society, 1950, p. 384,389
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1229,1231
  • 5
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  • [ 64965-48-6 ]
Reference: [1] Monatshefte fur Chemie, 2012, vol. 143, # 4, p. 619 - 623
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 2570,2573
[3] Patent: WO2011/22216, 2011, A1, . Location in patent: Page/Page column 30
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 17, p. 6871 - 6885
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Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2570,2573
[2] Patent: WO2011/22216, 2011, A1,
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  • [ 23833-99-0 ]
Reference: [1] Patent: US2013/210844, 2013, A1,
  • 8
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  • [ 50332-66-6 ]
YieldReaction ConditionsOperation in experiment
80.7% With nitric acid In propionic acid at 120℃; for 2.75 h; The first step: 5 g of 4-hydroxyquinoline of formula VI-1 (34.48 mmol, Purchased from Jiuding Chemical) dissolved in propionic acid (40mL, purity ≥99.5percent) and heated to 120°C; then, 3.5 mL of concentrated nitric acid diluted with propionic acid (41.38 mmol, The concentration of concentrated nitric acid is 65-68percent) slowly dropping in 1.5h, after about 15min, there is a yellow precipitate; Adding 20 mL of propionic acid followed by refluxing for 1 h. TLC (thin-layer chromatography) showed no 4-hydroxyquinoline as a reactant. The heating was stopped and the reaction solution was cooled to room temperature. The reaction solution was filtered, and the filter cake was washed with petroleum ether and vacuum-dried. The resulting yellow solid is 4-hydroxy-3-nitroquinoline of Formula V-1 (5.28 g, average yield 80.7percent),
76% With nitric acid In propionic acid for 3.66667 h; Reflux 4-Hydroxyquinoline (79.3 g) and propionic acid (790 mL) were combined and heated to 125° C. Nitric acid (79 mL) was added dropwise over 40 minutes. The reaction mixture was stirred at reflux temperature for a further 3 h and cooled to rt. The mixture was diluted with ethanol and the solid was collected by vacuum filtration. The solid was washed with ethanol, water then ethanol. The residue was refluxed in ethanol and the hot mixture was filtered and dried to give the subtitle compound (80.9 g). Yield: 76percent1H NMR δ (DMSO-d6) 13.00 (1H, s), 9.19 (1H, s), 8.26-8.23 (1H, m), 7.81-7.77 (1H, m), 7.75-7.71 (1H, m), 7.53-7.49 (1H, m)
71% at 20 - 125℃; EXAMPLE 15:
MOLECULE CL397
3-nitroquinolin-4-ol:
4-Hydroxyquinoline (20.0g, 138 mmol) was added to propionic acid (150 mL) and the solution was heated to about 125°C. Nitric acid (6.85 mL, 165 mmol) was added dropwise with stirring.
When the addition was complete, the mixture was stirred at about 125°C overnight.
Then the mixture was cooled to room temperature and was poured on ice.
The precipitated solid was filtered, washed sequentially with water, EtOH and Et2O, and dried to afford 3-nitro-4-hydroxyquinoline (18.7 g, yield 71percent) as a light yellow powder.
4-chloro-3-nitroquinoline:
65% at 125℃; Into a 1 00-mL round-bottom flask was placed a solution of quinolin-4-ol (4 g,27.56 mmol, 1.00 equiv) in CH3CH2COOH (30 mL). This was followed by the additionof HNO3 (1.77 mL). The resulting solution was stirred overnight at 125°C in an oil batch. The reaction mixture was cooled to room temperature and poured into water/ice. Theprecipitated solid was collected by filtration, washed with water and ethanol, and dried. This resulted in 3.414 g (65percent) of 3-nitroquinolin-4-ol as a yellow solid.LC-MS: (ES, m/z): [M+H] = 191.0
4.62 g With nitric acid; acetic acid In water for 0.25 h; Reflux 70percent Aqueous nitric acid (6.1 mL) was added dropwise to a mixture of 4- hydroxyquinoline (10 g, 69 mmol) and 100 mL of acetic acid heated at reflux. After 15 min, the mixture was allowed to cool to room temperature. Dilution with EtOH resulted in the formation of a precipitate, which was filtered and washed sequentially with EtOH, H20, and EtOH. Drying of the filtrate in vacuo gave 4.62 g of a light yellow powder. 1H NMR (DMSO-d6) δ 9.2 (s, 1H), 8.3 (d, 1H), 7.9-7.7 (m, 2H), 7.5 (m, 1H).

Reference: [1] Patent: US5367076, 1994, A,
[2] Patent: US5175296, 1992, A,
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3481 - 3491
[4] Patent: CN108003153, 2018, A, . Location in patent: Paragraph 0063; 0068
[5] Patent: US2011/136801, 2011, A1, . Location in patent: Page/Page column 21
[6] Patent: EP2674170, 2013, A1, . Location in patent: Paragraph 0227
[7] Patent: US2014/141033, 2014, A1, . Location in patent: Page/Page column
[8] Patent: WO2017/184735, 2017, A1, . Location in patent: Page/Page column 63
[9] Journal of the Chemical Society, 1949, p. 1367,1370
[10] Journal of the Chemical Society, 1950, p. 1130,1137
[11] Journal of the American Chemical Society, 1951, vol. 73, p. 2413,2414
[12] Patent: WO2003/97641, 2003, A2, . Location in patent: Page/Page column 50-51
[13] Patent: WO2014/120995, 2014, A2, . Location in patent: Page/Page column 172
[14] Patent: JP5837549, 2015, B2, . Location in patent: Paragraph 0100
[15] Patent: WO2008/135791, 2008, A1, . Location in patent: Page/Page column 48
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Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3481 - 3491
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 2413,2414
[3] Patent: US2011/136801, 2011, A1,
[4] Patent: EP2674170, 2013, A1,
[5] Patent: WO2014/120995, 2014, A2,
[6] Patent: JP5837549, 2015, B2,
[7] Patent: WO2017/184735, 2017, A1,
[8] Patent: CN108003153, 2018, A,
  • 10
  • [ 101273-58-9 ]
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13756 - 13767
  • 11
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Reference: [1] Patent: US4412076, 1983, A,
  • 12
  • [ 15568-92-0 ]
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Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 7, p. 738 - 743
  • 13
  • [ 2033-24-1 ]
  • [ 62-53-3 ]
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Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 6, p. 2232 - 2235
  • 14
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  • [ 611-36-9 ]
Reference: [1] Patent: US4412076, 1983, A,
[2] Patent: US4412076, 1983, A,
  • 15
  • [ 1613-37-2 ]
  • [ 4032-52-4 ]
  • [ 611-36-9 ]
  • [ 88237-18-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 6, p. 1833 - 1841
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  • [ 91-22-5 ]
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  • [ 119-91-5 ]
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Reference: [1] Russian Journal of Organic Chemistry, 1998, vol. 34, # 6, p. 905 - 905
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  • [ 79-36-7 ]
  • [ 4032-52-4 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 6, p. 1833 - 1841
  • 18
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Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 7, p. 738 - 743
  • 19
  • [ 23981-80-8 ]
  • [ 54-12-6 ]
  • [ 61-54-1 ]
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Reference: [1] Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 967 - 973
  • 20
  • [ 363-36-0 ]
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Reference: [1] Chemical and pharmaceutical bulletin, 2003, vol. 51, # 4, p. 409 - 411
[2] Toxicology Letters, 2017, vol. 272, p. 84 - 93
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Reference: [1] Photochemical and Photobiological Sciences, 2013, vol. 12, # 6, p. 967 - 973
  • 22
  • [ 529-37-3 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1982, vol. 324, # 3, p. 369 - 378
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  • [ 56-23-5 ]
  • [ 72812-97-6 ]
  • [ 7719-12-2 ]
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Reference: [1] Yakugaku Zasshi, 1955, vol. 75, p. 127[2] Chem.Abstr., 1956, p. 1817
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  • [ 67-66-3 ]
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Reference: [1] Yakugaku Zasshi, 1951, vol. 71, p. 263,265[2] Yakugaku Zasshi, 1955, vol. 75, p. 130,133[3] Chem.Abstr., 1956, p. 1817
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Reference: [1] Yakugaku Zasshi, 1955, vol. 75, p. 127[2] Chem.Abstr., 1956, p. 1817
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Reference: [1] Patent: EP1900732, 2008, A1,
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Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3481 - 3491
[2] Patent: WO2014/120995, 2014, A2,
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  • [ 99010-64-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 10, p. 3481 - 3491
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Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 37, p. 9311 - 9316[2] Angew. Chem., 2012, vol. 124, # 37, p. 9445 - 9450,6
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