[ CAS No. 59394-27-3 ]

Name: 59394-27-3|7-Chloroquinoline-2-carbaldehyde|98%
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Quality Control of [ 59394-27-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 59394-27-3 ]

Product Details of [ 59394-27-3 ]

CAS No. :	59394-27-3	MDL No. :	MFCD06407627
Formula :	C₁₀H₆ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LZJIPAFEFGRTQS-UHFFFAOYSA-N
M.W :	191.61	Pubchem ID :	1548875
Synonyms :

Calculated chemistry of [ 59394-27-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.14
TPSA :	29.96 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) :	-5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.52
Log Po/w (XLOGP3) :	2.77
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	1.7
Log Po/w (SILICOS-IT) :	3.22
Consensus Log Po/w :	2.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.28
Solubility :	0.101 mg/ml ; 0.000529 mol/l
Class :	Soluble
Log S (Ali) :	-3.05
Solubility :	0.169 mg/ml ; 0.000881 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.27
Solubility :	0.0103 mg/ml ; 0.000054 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.25

Safety of [ 59394-27-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 59394-27-3 ]

* 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.

Downstream synthetic route of [ 59394-27-3 ]

[ 59394-27-3 ] Synthesis Path-Downstream 1~30

1
[ 4965-33-7 ]
[ 59394-27-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With selenium(IV) oxide In 1,4-dioxane at 60℃; Inert atmosphere;
84%	With selenium(IV) oxide In 1,4-dioxane for 2.5h; Heating;
78%	With selenium(IV) oxide; water In tetrahydrofuran at 25℃; for 6h;

76%	With [bis(acetoxy)iodo]benzene In dimethyl sulfoxide at 120℃; for 0.5h; Microwave irradiation; Sealed tube; Green chemistry; regioselective reaction;	Experimental Procedures Typical experimental procedure for oxidation of 2-methylquinolines General procedure: Unless otherwise noted, reactions were carried out as following: 2-methylquinolines 1 (2 mmol), PIDA (4 mmol), DMSO(10 mL) were mixed in a sealed microwave tube. The reaction mixture was stirred at 120 °C for 30 min under microwave irradiation using a CEM Discover microwave reactor (the highest power: 85 W; run time: 10 min; hold time: 30 min; temperature: 120 °C). The resulting reaction mixture was neutralized with saturated aqueous NaHCO3 solution and extracted with Et2O. The combined organic layers were washed with H2O and dried over Na2SO4, then concentrated under reduced pressure. The crude residue was purified by flash chromatographyon silica gel using hexane/EtOAc as eluent.
62%	With copper(II) choride dihydrate; oxygen In N,N-dimethyl-formamide at 130℃; for 5h; Sealed tube;
	With V₂O₅#dotMoO₃; silica gel at 380 - 400℃; mit Wasserdampf und Luft;
	With iodine; dimethyl sulfoxide at 110℃; for 1h;	General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g.
	With iodine; dimethyl sulfoxide at 110℃; Sealed tube;	Standard procedure for the synthesis of 5-(quinolin-2-yl)-1,3,4-oxadiazoles General procedure: A 25 mL pressure vial was charged with 2-methylquinoline (1a) (71.5 mg, 0.50 mmol, 1.0 equiv.), I2 (317.3 mg, 1.25 mmol, 2.5 equiv.) and DMSO (3.0 mL). The vial was sealed and the resulting mixture was stirred at 110 °C for 4-6 h under an air atmosphere, after disappearance of the reactant (monitored by TLC), then added benzohydrazide (2a) (81.6 mg, 0.6 mmol, 1.2 equiv.) , K2CO3 (414.0 mg, 3.0 mmol, 6.0 equiv.) at 110 °C for another 4-6 h. After the reaction completed, and added 50 mL water to the mixture, then extracted with EtOAc 3 times (3 × 50 mL). The extract was washed with 10% Na2S2O3 solution (w/w), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was puried by flash column chromatography on silica gel to yield the corresponding product 3aa as a yellow solid (72% yield).
	With selenium(IV) oxide In 1,4-dioxane at 100℃;
	With iodine; dimethyl sulfoxide at 110℃; Sealed tube;
	With iodine; dimethyl sulfoxide; trifluoroacetic acid at 130℃; for 3h; Sealed tube;

Reference： [1]Dai, Chun-Guang; Du, Xiao-Jiao; Song, Qin-Hua [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12088 - 12099]
[2]Barbier, Christine; Joissains, Arnaud; Commercon, Alain; Riou, Jean-Francois; Huet, Francois [Heterocycles, 2000, vol. 53, # 1, p. 37 - 48]
[3]Saravanan; Satyanarayana; Reddy, P. Pratap [Synthetic Communications, 2013, vol. 43, # 15, p. 2050 - 2056]
[4]Jiang, Long; Huang, Yingyi; Yan, Yiyan; Xie, Yuanyuan [Tetrahedron Letters, 2016, vol. 57, # 37, p. 4149 - 4151]
[5]Zheng, Gang; Liu, Hao; Wang, Mang [Chinese Journal of Chemistry, 2016, vol. 34, # 5, p. 519 - 523]
[6]Mathes; Sauermilch [Chemische Berichte, 1957, vol. 90, p. 758,761]
[7]Baig, Mirza Feroz; Shaik, Siddiq Pasha; Nayak, V. Lakshma; Alarifi, Abdullah; Kamal, Ahmed [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 17, p. 4039 - 4043]
[8]Shang, Zhi-Hao; Sun, Ji-Na; Guo, Jiang-Shan; Sun, Yuan-Yuan; Weng, Wei-Zhao; Zhang, Zhen-Xiao; Li, Zeng-Jing; Zhu, Yan-Ping [Tetrahedron, 2020, vol. 76, # 6]
[9]Zhou, Tongtong; He, Xinwei; Zuo, Youpeng; Wu, Yuhao; Hu, Wangcheng; Zhang, Shiwen; Duan, Jiahui; Shang, Yongjia [Chinese Journal of Chemistry, 2021, vol. 39, # 3, p. 621 - 626]
[10]Hu, Qi-Qi; Gao, Yan-Ting; Sun, Jia-Chen; Gao, Jing-Jing; Mu, Hong-Xiao; Li, Yi-Ming; Zheng, Ya-Nan; Yang, Kai-Rui; Zhu, Yan-Ping [Organic Letters, 2021, vol. 23, # 22, p. 9000 - 9005]
[11]Zhang, Xin-Ke; Miao, Xiao-Yu; Zhou, Yu; Wang, Yu-Mei; Song, Ying-Chun; Liu, Hang; Xiong, Yi-Lu; Li, Ling-Yu; Wu, An-Xin; Zhu, Yan-Ping [Organic and Biomolecular Chemistry, 2022, vol. 20, # 6, p. 1236 - 1242]

2
[ 59394-27-3 ]
[ 260430-95-3 ]
[ 260431-06-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	With pyridinium p-toluenesulfonate In toluene for 8h; Heating;

Reference： [1]Barbier, Christine; Joissains, Arnaud; Commercon, Alain; Riou, Jean-Francois; Huet, Francois [Heterocycles, 2000, vol. 53, # 1, p. 37 - 48]

3
[ 59394-27-3 ]
[ 4299-70-1 ]
[ 260430-98-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With pyridinium p-toluenesulfonate In toluene for 10h; Heating;

Reference： [1]Barbier, Christine; Joissains, Arnaud; Commercon, Alain; Riou, Jean-Francois; Huet, Francois [Heterocycles, 2000, vol. 53, # 1, p. 37 - 48]

Yield	Reaction Conditions	Operation in experiment
	entspr. 2-CH3-Chinolin Ig, SeO2;

5
[ 59394-27-3 ]
1-(7-chloro-quinolin-2-yl)-9<i>H</i>-β-carboline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 60 percent / pyridinium tosylate / toluene / 10 h / Heating 2: 68 percent / NaOH / H₂O; methanol / 4 h / Heating

Reference： [1]Barbier, Christine; Joissains, Arnaud; Commercon, Alain; Riou, Jean-Francois; Huet, Francois [Heterocycles, 2000, vol. 53, # 1, p. 37 - 48]

6
[ 59394-27-3 ]
1-(7-chloro-quinolin-2-yl)-8-methyl-9<i>H</i>-β-carboline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 48 percent / pyridinium tosylate / toluene / 8 h / Heating 2: 80 percent / NaOH / H₂O; methanol / 3.5 h / Heating

Reference： [1]Barbier, Christine; Joissains, Arnaud; Commercon, Alain; Riou, Jean-Francois; Huet, Francois [Heterocycles, 2000, vol. 53, # 1, p. 37 - 48]

7
[ 59394-27-3 ]
[ 1830-54-2 ]
[ 74-89-5 ]
[ 1046862-13-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	In methanol; water at 0 - 20℃;

Reference： [1]Location in patent: experimental part Comba, Peter; Lang, Carolin; De Laorden, Carlos Lopez; Muruganantham, Amsaveni; Rajaraman, Gopalan; Wadepohl, Hubert; Zajaczkowski, Marta [Chemistry - A European Journal, 2008, vol. 14, # 17, p. 5313 - 5328]

8
[ 59394-27-3 ]
[ 1426679-10-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: methanol / 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / 3.17 h / 0 - 20 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4.1: 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / dichloromethane / 16 h / 20 °C / Inert atmosphere; Schlenk technique

Reference： [1]Wang, Shou-Guo; Zhang, Wei; You, Shu-Li [Organic Letters, 2013, vol. 15, # 7, p. 1488 - 1491]

9
[ 59394-27-3 ]
[ 1426679-00-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: methanol / 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / 3.17 h / 0 - 20 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere

Reference： [1]Wang, Shou-Guo; Zhang, Wei; You, Shu-Li [Organic Letters, 2013, vol. 15, # 7, p. 1488 - 1491]

10
[ 59394-27-3 ]
[ 1426678-85-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: methanol / 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / 3.17 h / 0 - 20 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Wang, Shou-Guo; Zhang, Wei; You, Shu-Li [Organic Letters, 2013, vol. 15, # 7, p. 1488 - 1491]

11
[ 21109-25-1 ]
[ 59394-27-3 ]
C₁₉H₁₄ClN₃ [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1488 - 1491

12
[ 59394-27-3 ]
[ 158966-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C 1.2: 4 h / 0 - 15 °C 2.1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 110 °C 3.1: caustic lye / 12 h / 120 °C

Reference： [1]Saravanan; Satyanarayana; Reddy, P. Pratap [Synthetic Communications, 2013, vol. 43, # 15, p. 2050 - 2056]

13
[ 59394-27-3 ]
[ 151767-02-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 5 °C 1.2: 4 h / 0 - 15 °C 2.1: palladium diacetate; triphenylphosphine; triethylamine / N,N-dimethyl-formamide / 110 °C 3.1: caustic lye / 12 h / 120 °C 4.1: sodium hydroxide / methanol / 1 h / 25 °C

Reference： [1]Saravanan; Satyanarayana; Reddy, P. Pratap [Synthetic Communications, 2013, vol. 43, # 15, p. 2050 - 2056]

14
[ 59394-27-3 ]
[ 1779-49-3 ]
[ 177748-00-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Stage #2: 7-chloro-quinoline-2-carbaldehyde In tetrahydrofuran; hexane; dichloromethane at 0 - 15℃; for 4h;

Reference： [1]Saravanan; Satyanarayana; Reddy, P. Pratap [Synthetic Communications, 2013, vol. 43, # 15, p. 2050 - 2056]

15
[ 59394-27-3 ]
[ 105-53-3 ]
diethyl 2-((7-chloroquinolin-2-yl)methylene)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With piperidine In ethanol at 50℃; for 12h; Inert atmosphere;

Reference： [1]Dai, Chun-Guang; Du, Xiao-Jiao; Song, Qin-Hua [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12088 - 12099]

16
[ 108-42-9 ]
[ 59394-27-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: hydrogenchloride / water; toluene / 1.5 h / 110 °C 1.2: 1 h / 60 °C / Cooling with ice 2.1: selenium(IV) oxide / 1,4-dioxane / 60 °C / Inert atmosphere

Reference： [1]Dai, Chun-Guang; Du, Xiao-Jiao; Song, Qin-Hua [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12088 - 12099]

17
[ 59394-27-3 ]
2-((7-chloroquinolin-2-yl)methylene)malonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: piperidine / ethanol / 12 h / 50 °C / Inert atmosphere 2: potassium hydroxide / water; ethanol / 2 h / 80 °C / Inert atmosphere

Reference： [1]Dai, Chun-Guang; Du, Xiao-Jiao; Song, Qin-Hua [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12088 - 12099]

18
[ 59394-27-3 ]
C₁₆H₁₅ClN₂O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: piperidine / ethanol / 12 h / 50 °C / Inert atmosphere 2: potassium hydroxide / water; ethanol / 2 h / 80 °C / Inert atmosphere 3: 20 °C / pH 3

Reference： [1]Dai, Chun-Guang; Du, Xiao-Jiao; Song, Qin-Hua [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12088 - 12099]

19
[ 59394-27-3 ]
[ 95-54-5 ]
2-(1H-benzo[d]imidazol-2-yl)-7-chloroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 110℃; for 7h;	General Procedure General procedure: In a 25 mL round bottom flask equipped with a magnetic stir bar, The 2-methylquinoline (80 mg, 0.56 mmol) was dissolved in DMSO (4 mL) and molecular iodine (20 mol%)) was added and heated at 110 °C for 1 h. Next, o-phenylenediamine (0.56 mmol) was added and the resulting solution stirred continuous for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with saturated solution of Na2S2O3 (20 mL) and the reaction was extracted with ethyl acetate (3x 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using Petroleum ether as eluent to provide 3a-u and 5a-g.