[ CAS No. 580-20-1 ] {[proInfo.proName]}

Name: 580-20-1|Quinolin-7-ol|98%
Brand: Ambeed
SKU: A210867
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Quality Control of [ 580-20-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 580-20-1 ]

SDS Specification

Alternatived Products of [ 580-20-1 ]

Product Details of [ 580-20-1 ]

CAS No. :	580-20-1	MDL No. :	MFCD00016730
Formula :	C₉H₇NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XCRPPAPDRUBKRJ-UHFFFAOYSA-N
M.W :	145.16	Pubchem ID :	135426866
Synonyms :

Calculated chemistry of [ 580-20-1 ]

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 Å²

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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.42
Log Po/w (XLOGP3) :	1.98
Log Po/w (WLOGP) :	1.94
Log Po/w (MLOGP) :	1.19
Log Po/w (SILICOS-IT) :	2.01
Consensus Log Po/w :	1.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.66
Solubility :	0.317 mg/ml ; 0.00219 mol/l
Class :	Soluble
Log S (Ali) :	-2.3
Solubility :	0.725 mg/ml ; 0.005 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 :	1.12

Safety of [ 580-20-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 580-20-1 ]

* 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 [ 580-20-1 ]
Downstream synthetic route of [ 580-20-1 ]

[ 580-20-1 ] Synthesis Path-Upstream 1~26

1
[ 333383-93-0 ]
[ 580-20-1 ]

Reference： [1] Patent: US2004/34217, 2004, A1, . Location in patent: Page 5
[2] Organic Process Research and Development, 2006, vol. 10, # 1, p. 149 - 152

2
[ 58196-33-1 ]
[ 580-20-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5487 - 5491[2] Angew. Chem., 2018, vol. 130, # 19, p. 5585 - 5589,5
[3] Advanced Synthesis and Catalysis, 2017, vol. 359, # 14, p. 2358 - 2363

3
[ 3054-95-3 ]
[ 591-27-5 ]
[ 580-20-1 ]

Yield	Reaction Conditions	Operation in experiment
31.3 %Chromat.	With Ni-modified Beta zeolite In neat (no solvent) for 0.0833333 h; Microwave irradiation; Reflux; Green chemistry	General procedure: General procedure for synthesis of quinolines from anilines and ADA was carried out in Panasonic NN-K5541JF microwave oven reactor equipping a magnetic stirring device. The typical procedures were as follows: ADA (1mmol), excessive anilines (4mmol) and solid catalyst were charged into a round-bottom ask; and then, the mixtures was placed into microwave reactor. The reaction was conducted by continuous microwave irradiation for 1–40 min under refluxing and stirring condition. Finally, the resulting products were determined by GC–MS of Varian Saturn 2200/ CP-3800 gas chromatography–mass spectrometry equipped with two CP8944 capillary columns (VF-5,30m×0.25mm×0.25 μm).

Reference： [1] Catalysis Communications, 2018, vol. 115, p. 21 - 25

4
[ 56-81-5 ]
[ 591-27-5 ]
[ 580-20-1 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 41, p. 21456 - 21464
[2] Journal of the Chemical Society, 1947, p. 437,44

5
[ 591-27-5 ]
[ 107-02-8 ]
[ 580-20-1 ]

Reference： [1] Patent: WO2006/2473, 2006, A1, . Location in patent: Page/Page column 48

6
[ 4964-76-5 ]
[ 580-20-1 ]
[ 128278-08-0 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 10.2, p. 1890 - 1896[2] Zhurnal Organicheskoi Khimii, 1990, vol. 26, # 10, p. 2191 - 2198

7
[ 3743-29-1 ]
[ 580-20-1 ]

Reference： [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
[2] Organic Process Research and Development, 2006, vol. 10, # 1, p. 149 - 152
[3] Organic Process Research and Development, 2006, vol. 10, # 1, p. 149 - 152

8
[ 591-27-5 ]
[ 580-20-1 ]

9
[ 4964-76-5 ]
[ 580-20-1 ]

Reference： [1] Journal of the American Chemical Society, 1946, vol. 68, p. 1562

10
[ 333383-80-5 ]
[ 580-20-1 ]
[ 578-67-6 ]

Reference： [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108

11
[ 580-19-8 ]
[ 580-20-1 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 45, p. 238[2] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 176
[3] Journal fuer Praktische Chemie (Leipzig), 1892, vol. <2> 45, p. 238[4] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 176

12
[ 554-84-7 ]
[ 591-27-5 ]
[ 580-20-1 ]

Reference： [1] Chemische Berichte, 1887, vol. 20, p. 2174
[2] Monatshefte fuer Chemie, 1882, vol. 3, p. 551[3] Monatshefte fuer Chemie, 1883, vol. 4, p. 698
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 178
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 179

13
[ 333383-80-5 ]
[ 580-20-1 ]

Reference： [1] Organic Process Research and Development, 2006, vol. 10, # 1, p. 149 - 152

14
[ 81336-60-9 ]
[ 580-20-1 ]
[ 65-85-0 ]

Reference： [1] Tetrahedron Letters, 1981, vol. 22, # 47, p. 4733 - 4736

15
[ 554-84-7 ]
[ 56-81-5 ]
[ 580-20-1 ]

Reference： [1] Journal of the Indian Chemical Society, 1952, vol. 29, p. 711
[2] Journal of the Indian Chemical Society, 1952, vol. 29, p. 711

16
[ 110288-09-0 ]
[ 580-20-1 ]
[ 148-24-3 ]

Reference： [1] Tetrahedron Letters, 1986, vol. 27, # 36, p. 4253 - 4256

17
[ 591-27-5 ]
[ 124521-13-7 ]
[ 580-20-1 ]

Reference： [1] Chemical Research in Toxicology, 1995, vol. 8, # 4, p. 515 - 524

18
[ 591-27-5 ]
[ 140226-30-8 ]
[ 580-20-1 ]

Reference： [1] Chemical Research in Toxicology, 1995, vol. 8, # 4, p. 515 - 524

19
[ 591-27-5 ]
[ 140226-31-9 ]
[ 580-20-1 ]

Reference： [1] Chemical Research in Toxicology, 1995, vol. 8, # 4, p. 515 - 524

20
[ 81123-52-6 ]
[ 580-20-1 ]

Reference： [1] Chemical Physics Letters, 1995, vol. 235, # 5,6, p. 463 - 470

21
[ 333383-80-5 ]
[ 580-20-1 ]
[ 578-67-6 ]

Reference： [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108

22
[ 580-20-1 ]
[ 74-88-4 ]
[ 4964-76-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1 h; Stage #2: at 20℃; for 1 h;	To a solution of sodium hydride (5.5 g, 137.50 mmol, 60percent) in N,N-dimethylformamide (150 ml) was added quinolin-7-ol (8 g, 55.1 1 mmol). The reaction was stirred for 1 h at 0°C in a water/ice bath. Then CH₃I (7.84 g, 55.23 mmol) was added and the solution was stirred for an additional 1 h at room temperature. The reaction was then quenched by the addition of water/ice (700 ml) and extracted with ethyl acetate (3 x 200 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a residue, which was purified by a silica gel column with 6 percent ethyl acetate in petroleum ether to afford 7-methoxyquinoline as a red oil (5.5 g, 63percent).LC/MS (ES, m/z): [M+H]+ 160.0'H-NMR (300 MHz, CDC13): δ 8.84 - 8.86 (m, 1H), 8.07 - 8.11 (m, 1H), 7.70 - 7.73 (t, / = 5.1 Hz, 1H), 7.44 (d, / = 2.4 Hz, 1H), 7.20 - 7.30 (m, 2H), 3.95 (s, 3H) Attorney Docket No. BIOE0009-401-PC
25%	With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12 h; Inert atmosphere	To a solution of quinolin-7-ol (5 g, 34.44 mmol) and Cs2CO3 (22.46 g, 68.89 mmol) in DMF (50 mL) was added iodomethane (2.1 mL, 34.44 mmol). The mixture was stirred at 20 °C for12 b under a nitrogen atmosphere. Water (100 mL) was added and the mixture was extracted with EtOAc (5OmL x 3). The combined organic layers were washed with brine (100 mE x 3), dried over anhydrous Na2SO4 and concentrated in vacuo. The cmde residue was purified by silica gel chromatography (petroleum ether EtOAc = 10: 1) to give the title compound (2.0 g, 25percent) as a yellow oil.

Reference： [1] Synthetic Communications, 2000, vol. 30, # 2, p. 367 - 375
[2] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 82
[3] Patent: WO2016/86200, 2016, A1, . Location in patent: Page/Page column 278
[4] Patent: WO2012/58125, 2012, A1, . Location in patent: Page/Page column 115; 116

23
[ 580-20-1 ]
[ 90224-71-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bromine; acetic acid In dichloromethane at 0 - 5℃;	Step 2: 8-Bromo-7-hydroxyquinoline[0152] To a stirred solution of 7-hydroxyquinoline (59.0 g, 0.406 mol) in AcOH (120 mL) and CH₂Cl₂ (240 mL) was slowly added bromine (22.9 ml, 0.444 mol) in AcOH (120 ml) while keeping the internal temperature at 0 - 5 ⁰C. The resulting suspension was stirred for 2 h at 0^~5 ⁰C, and thendiluted with EtOAc (100 rnL) and filtered. The solid was washed withEtOAc (2 x 20 mL) and dried in vacuo to give 8-bromo-7-hydroxyquinoline (65 g, 76percent).

Reference： [1] Patent: WO2010/54006, 2010, A1, . Location in patent: Page/Page column 52-53
[2] Yakugaku Zasshi, 1955, vol. 75, p. 28[3] Chem.Abstr., 1956, p. 1021

24
[ 580-20-1 ]
[ 58196-33-1 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 14, p. 4159 - 4163
[2] Helvetica Chimica Acta, 1949, vol. 32, p. 1278,1281
[3] Journal of the American Chemical Society, 1944, vol. 66, p. 1166,1168
[4] New Journal of Chemistry, 2018, vol. 42, # 20, p. 16694 - 16702

25
[ 580-20-1 ]
[ 7664-93-9 ]
[ 7732-18-5 ]
[ 58196-33-1 ]

Reference： [1] Helvetica Chimica Acta, 1949, vol. 32, p. 1278,1281

26
[ 580-20-1 ]
[ 19500-61-9 ]

Reference： [1] Patent: WO2012/94462, 2012, A2,
[2] Patent: WO2016/86200, 2016, A1,
[3] Patent: WO2012/58125, 2012, A1,

[ 580-20-1 ] Synthesis Path-Downstream 1~77

1
[ 580-20-1 ]
[ 67-66-3 ]
[ 82070-00-6 ]

Yield	Reaction Conditions	Operation in experiment
6%	With sodium hydroxide; In water; at 92℃; for 20h;	To a stirred solution of <strong>[580-20-1]7-hydroxyquinoline</strong> (4.00 g, 27.5 mmol) in CHCl3 (60.0 mL) was added a solution of NaOH (27.6 g, 689 mmol) in water (30 mL). The resulting mixture was stirred for 20 h at 92 C. The reaction mixture was poured into water (100 mL) and the resulting mixture was then extracted with dichloromethane (3 x 100mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by reverse phase chromatography (column, C18 silica gel; mobile phase A: water (containing 10 mmol/L NH4HCO3) and B: MeCN (5% to 90% over 30 min); Flow rate: 60 mL/min; Detector: UV 254/220 nm). The product fractions were concentrated under vacuum to afford <strong>[580-20-1]7-hydroxyquinoline</strong>-8-carbaldehyde (300 mg, 6%) as a light yellow solid. LCMS (ES, m/z): 174 [M+H]+.
200 mg	With sodium hydroxide; In water; at 92℃; for 20h;	To a solution of Example 55a (2 g, 13.8 mmol) in chloroform (30 mL) an aqueous NaOH (16 mL, 350 mmol) solution was added. The resulting mixture was stirred at 92C for 20hrs until TLC indicated complete conversion and athick, dark brown, frothing liquid was show. The reaction was diluted with water (300 mL), and then extracted with DCM (200 mL*3) and combined the organic phase, washed with brine, dried over Na2S04. Concentration in vacuum to give the crude desired product which was further purified by silica gel chromatography to afford the desired product (Example 55b, 200 mg) as a yellow solid.

Reference： [1]Patent: WO2020/23802,2020,A1 .Location in patent: Paragraph 0601; 0615; 0616
[2]Chemische Berichte,1936,vol. 69,p. 1807,1812
[3]Patent: WO2017/218960,2017,A1 .Location in patent: Paragraph 00583

2
[ 580-20-1 ]
[ 90224-71-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bromine; acetic acid; In dichloromethane; at 0 - 5℃;	Step 2: 8-Bromo-7-hydroxyquinoline[0152] To a stirred solution of 7-hydroxyquinoline (59.0 g, 0.406 mol) in AcOH (120 mL) and CH2Cl2 (240 mL) was slowly added bromine (22.9 ml, 0.444 mol) in AcOH (120 ml) while keeping the internal temperature at 0 - 5 0C. The resulting suspension was stirred for 2 h at 0~5 0C, and thendiluted with EtOAc (100 rnL) and filtered. The solid was washed withEtOAc (2 x 20 mL) and dried in vacuo to give 8-bromo-7-hydroxyquinoline (65 g, 76%).

Reference： [1]Patent: WO2010/54006,2010,A1 .Location in patent: Page/Page column 52-53
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1955,vol. 75,p. 28
Chem.Abstr.,1956,p. 1021

3
[ 580-20-1 ]
[ 58196-33-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium cyanoborohydride; In ethanol; at 20℃; for 4h;	To a solution of 7-hydroxyquinoline (2 g, 13.8 mmol) in 30 mL EtOH is added NaCNBH3 (3.5 g, 55 mmol) in portions. After stirring at room temperature for 4 hr, the mixture is concentrated, extracted with EtOAc, and washed with brine. The organic layer is dried over Na2SO4 and evaporated. The crude product is purified on silica gel using hexane/EtOAc. Yield: 1.44 g (70%).

Reference： [1]Organic Letters,2018,vol. 20,p. 4159 - 4163
[2]Patent: US10513610,2019,B1 .Location in patent: Page/Page column 11-12
[3]Helvetica Chimica Acta,1949,vol. 32,p. 1278,1281
[4]Journal of the American Chemical Society,1944,vol. 66,p. 1166,1168
[5]New Journal of Chemistry,2018,vol. 42,p. 16694 - 16702

4
[ 580-19-8 ]
[ 580-20-1 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1892,vol. <2> 45,p. 238
Journal fuer Praktische Chemie (Leipzig),1893,vol. <2> 48,p. 176
[2]Journal fur praktische Chemie (Leipzig 1954),1892,vol. <2> 45,p. 238
Journal fuer Praktische Chemie (Leipzig),1893,vol. <2> 48,p. 176

5
[ 4964-76-5 ]
[ 580-20-1 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1562

6
[ 56-81-5 ]
[ 591-27-5 ]
[ 580-20-1 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 21456 - 21464
[2]Journal of the Chemical Society,1947,p. 437,44

7
[ 580-20-1 ]
[ 700-87-8 ]
[ 100926-74-7 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 62 - 67

8
[ 580-20-1 ]
[ 5416-93-3 ]
[ 100926-71-4 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 62 - 67

9
[ 580-20-1 ]
[ 614-68-6 ]
[ 100926-80-5 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 62 - 67

10
[ 580-20-1 ]
[ 93499-67-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 20℃; for 3h;	Into a 100-mL round-bottom flask was placed <strong>[580-20-1]quinolin-7-ol</strong> (4 g, 28 mmol), ethyl acetate (60 mL) and m-chloroperoxybenzoic acid (7.1 g, 41 mmol). The solution was stirred at room temperature for 3 hours, then saturated sodium bicarbonate (60 mL) was added. A solid remained suspended which was filtered off and dried to yield <strong>[580-20-1]7-hydroxyquinoline</strong> 1-oxide (3.6 g, 81%).

Reference： [1]Heterocycles,1999,vol. 50,p. 453 - 462
[2]Patent: WO2019/200120,2019,A1 .Location in patent: Paragraph 000517
[3]Chemistry of Heterocyclic Compounds,1981,vol. 17,p. 72 - 76
Khimiya Geterotsiklicheskikh Soedinenii,1981,p. 89 - 94
[4]Chemical Communications,2013,vol. 49,p. 6900 - 6902

11
[ 4964-76-5 ]
[ 580-20-1 ]
[ 128278-08-0 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1990,vol. 26,p. 1890 - 1896
Zhurnal Organicheskoi Khimii,1990,vol. 26,p. 2191 - 2198

12
[ 580-20-1 ]
[ 79-44-7 ]
[ 115581-03-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With pyridine; at 100℃; for 48h;	[0070] Without being bound by theory, failure of the coupling reactions is believed to arise from the poisoning of the metal by the basic nitrogen atom. Accordingly the established Ullmann coupling strategy was selected as an alternative way to construct the biaryl system. When MeI was used to conduct methylation of 4, only trace of mono methylation product was observed. Under microwave conditions, the messy complex was formed. This condition is to be further optimized. Starting from the <strong>[580-20-1]7-hydoxyquinoline</strong>, under the protection of dimethylaminocarbonyl chloride to give carbamate 2 in 90% yield. Direct ortho metalation of carbamate 2 was carried out with LDA in THF at -78 0C, after which a solution of iodine in THF was added to the resulting metalate at -78 0C to afford 8-iodoquinoline 3 in 40 % yield. Ullmann coupling of iodide 3 with copper catalyst proceeded in 60 % yield to produce biaryl 4. The quinoline part of 4 was effectively reduced to give biquinolyl 5 quantitatively in the presence of ammonium formate and Pd/C. Methylation of the amine ensured using potassium carbonate as base, and finally culminating at basic methanolysis of the carbamate groups of 5 to afford the target molecule 7 in good yield (Fig. 4).

Reference： [1]Organic Letters,2009,vol. 11,p. 2876 - 2879
[2]Patent: WO2010/132029,2010,A1 .Location in patent: Page/Page column 24-25; 3/13
[3]Journal of Organic Chemistry,2005,vol. 70,p. 373 - 376
[4]Journal of Organometallic Chemistry,1987,vol. 336,p. 1 - 12

13
[ 580-20-1 ]
[ 542-69-8 ]
7-butoxyquinoline [ No CAS ]