[ CAS No. 659730-27-5 ] {[proInfo.proName]}

Name: 659730-27-5|7-Hydroxyquinoline-3-carboxylic acid|95%
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SKU: A294594
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Quality Control of [ 659730-27-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 659730-27-5 ]

SDS Specification

Alternatived Products of [ 659730-27-5 ]

Product Details of [ 659730-27-5 ]

CAS No. :	659730-27-5	MDL No. :	MFCD18417142
Formula :	C₁₀H₇NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RFVSBXGQVAGYJQ-UHFFFAOYSA-N
M.W :	189.17	Pubchem ID :	136107611
Synonyms :

Calculated chemistry of [ 659730-27-5 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.73
TPSA :	70.42 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.11
Log Po/w (XLOGP3) :	1.36
Log Po/w (WLOGP) :	1.64
Log Po/w (MLOGP) :	-0.35
Log Po/w (SILICOS-IT) :	1.31
Consensus Log Po/w :	1.01

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.33
Solubility :	0.88 mg/ml ; 0.00465 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.685 mg/ml ; 0.00362 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.5
Solubility :	0.597 mg/ml ; 0.00316 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.22

Safety of [ 659730-27-5 ]

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

Application In Synthesis of [ 659730-27-5 ]

* 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 [ 659730-27-5 ]
Downstream synthetic route of [ 659730-27-5 ]

[ 659730-27-5 ] Synthesis Path-Upstream 1~6

1
[ 71083-49-3 ]
[ 659730-27-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: for 12 h; Heating / reflux Stage #2: With potassium hydroxide In water at 20℃;	Stage A: 7-hydroxy 3-quinolinecarboxylic acid. A solution of 3-cyano-7-methoxyquinoline (2Og, 1 10 mmol) [described in Tetrahedron Lett.1998, 39 (23), 4013-4016] in 48percent aqueous solution bromhydric acid (300 ml) is stirred and heated under reflux for 12 hours. The reaction mixture was then cooled to room temperature and neutralised by adding 20percent aqueous KOH. The resulting precipitate was filtered and dried under vacuum. In this way 15.2 g (yield: 73percent) of the product of molecular formula CioH₇Nψ₃ was recovered. Aspect: brown powder.Melting point: >260°C.NMR spectrum of the protonIn DMSO-J₆ at 300MHz, chemical shifts (ppm) and multiplicity: 13.28 (s, 1 H), 10.68 (s, 1H), 9.20 (d, J= 2 Hz, 1 H), 8.84 (d, J= 2 Hz, 1 H), 8.06 (d, J = 9 Hz, 1 H), 7.34 (s, 1 H), 7.29 (d,J= 9 Hz, 1 H).

Reference： [1] Patent: WO2006/103120, 2006, A2, . Location in patent: Page/Page column 42
[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 12, p. 2612 - 2618

2
[ 71082-46-7 ]
[ 659730-27-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogen bromide In water at 105℃; for 88.5 h;	Step E. 7-Hydroxyquinoline-3-carboxylic acid. Ethyl 7-methoxyquinoline-3-carboxylate (7.03 g, 30.4 mmol) was dissolved in HBr (48percent aq., 150 mL) and was heated at 105° C. for 88.5 h. The reaction was cooled to ambient temperature and the precipitate was collected by filtration to afford the title compound as a brown solid (5.2 g, 90percent). ¹H NMR (400 MHz, DMSO-d₆) δ 12.05-11.67 (m, 1H), 9.49 (d, J=2.0 Hz, 1H), 9.43 (s, 1H), 8.39 (d, J=9.8 Hz, 1H), 7.55-7.51 (m, 2H). [M+H]=190.2.

Reference： [1] Patent: US2014/275548, 2014, A1, . Location in patent: Paragraph 0363

3
[ 63463-15-0 ]
[ 659730-27-5 ]

Reference： [1] Patent: US2014/275548, 2014, A1,

4
[ 536-90-3 ]
[ 659730-27-5 ]

Reference： [1] Patent: US2014/275548, 2014, A1,

5
[ 56881-19-7 ]
[ 659730-27-5 ]

Reference： [1] Patent: US2014/275548, 2014, A1,

6
[ 77156-85-5 ]
[ 659730-27-5 ]

Reference： [1] Patent: US2014/275548, 2014, A1,

[ 659730-27-5 ] Synthesis Path-Downstream 1~9

1
[ 659730-27-5 ]
[ 64-17-5 ]
ethyl 7-hydroxyquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		Stage B: ethyl 7-hydroxyquinoline-3-carboxylateTo a solution of the compound obtained in stage A (15 g, 79 mmol) in EtOH (500 ml) was added dropwise SOCl2 (40 mL). The resulting mixture was stirred under reflux during 12 hours. After adding water (200 mL), the pH was adjusted to 7.0 with 20% aqueous Na2COj. The aqueous solution was extracted with CH2Cl2 (3 x 200 mL). The combined organic layers were dried over MgSO4, filtered and evaporated to afford 1 1 g (yield: 64%) of the product of molecular formula CnHnNOy Aspect: pale brown powder.Melting point: 182C.NMR spectrum of the proton In CDCl3, at 300MHz, chemicals shifts (ppm) and multiplicity: 9.24 (d, J = 2 Hz, 1 H), 8.70(d, J = 2 Hz, 1 H), 7.66 (d, 9 Hz, 1 H), 7.36 (s, 1 H), 7.02 (dd, J = 9 and 2 Hz, 1 H), 4.48 (q, J= 7.1 Hz, 2 H), 1.48 (t, J = 7.1 Hz, 3 H).
58%	With sulfuric acid; at 75.0℃;	Step F. Ethyl 7-hydroxyquinoline-3-carboxylate. To a solution of <strong>[659730-27-5]7-hydroxyquinoline-3-carboxylic acid</strong> (273 mg, 1.44 mmol) in ethanol (6.0 mL) was added H2SO4 (60 muL). The reaction was heated at 75 C. overnight. After cooling to ambient temperature the reaction was concentrated onto silica gel. Purification by FCC (SiO2, 0-10% MeOH/DCM) afforded the title compound as a yellow solid (181 mg, 58%). 1H NMR (400 MHz, DMSO-d6) delta 10.70 (s, 1H), 9.20 (d, J=2.3 Hz, 1H), 8.86 (d, J=2.0 Hz, 1H), 8.08 (d, J=8.6 Hz, 1H), 7.33 (d, J=2.7 Hz, 1H), 7.28 (dd, J=9.0, 2.3, Hz, 1H), 4.41 (q, J=7.3 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H). [M+H]=218.2.

Reference： [1]Patent: WO2006/103120,2006,A2 .Location in patent: Page/Page column 42
[2]Organic and Biomolecular Chemistry,2009,vol. 7,p. 2612 - 2618
[3]Patent: US2014/275548,2014,A1 .Location in patent: Paragraph 0364

2
[ 71083-49-3 ]
[ 659730-27-5 ]

Yield	Reaction Conditions	Operation in experiment
73%		Stage A: 7-hydroxy 3-quinolinecarboxylic acid. A solution of 3-cyano-7-methoxyquinoline (2Og, 1 10 mmol) [described in Tetrahedron Lett.1998, 39 (23), 4013-4016] in 48% aqueous solution bromhydric acid (300 ml) is stirred and heated under reflux for 12 hours. The reaction mixture was then cooled to room temperature and neutralised by adding 20% aqueous KOH. The resulting precipitate was filtered and dried under vacuum. In this way 15.2 g (yield: 73%) of the product of molecular formula CioH7Ntheta3 was recovered. Aspect: brown powder.Melting point: >260C.NMR spectrum of the protonIn DMSO-J6 at 300MHz, chemical shifts (ppm) and multiplicity: 13.28 (s, 1 H), 10.68 (s, 1H), 9.20 (d, J= 2 Hz, 1 H), 8.84 (d, J= 2 Hz, 1 H), 8.06 (d, J = 9 Hz, 1 H), 7.34 (s, 1 H), 7.29 (d,J= 9 Hz, 1 H).

Reference： [1]Patent: WO2006/103120,2006,A2 .Location in patent: Page/Page column 42
[2]Organic and Biomolecular Chemistry,2009,vol. 7,p. 2612 - 2618

4
[ 659730-27-5 ]
ethyl 7-[(4-chlorophenyl)methoxy]quinoline-3-carboxylate [ No CAS ]