Name: 139549-06-7|2-Methoxyquinoline-3-carbaldehyde|98+%
Brand: Ambeed
SKU: A307387
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1
[ 139549-06-7 ]
1-(4-nitro-3-trimethylsilanylmethyl-phenoxy)-propan-2-one [ No CAS ]
1-{3-[2-hydroxy-2-(2-methoxy-quinolin-3-yl)-ethyl]-4-nitro-phenoxy}-propan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.90 g	With tetrabutyl ammonium fluoride In Isopropyl acetate at 20℃; for 0.5h;

Reference： [1]Wong, Audrey; Kuethe, Jeffrey T.; Davies, Ian W. [Journal of Organic Chemistry, 2003, vol. 68, # 25, p. 9865 - 9866]

2
[ 139549-06-7 ]
[ 616882-56-5 ]
[ 616882-64-5 ]

Yield	Reaction Conditions	Operation in experiment
	With Isopropyl acetate; tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Davies, Ian W. [Organic Letters, 2003, vol. 5, # 21, p. 3975 - 3978]

3
[ 139549-06-7 ]
[ 616882-52-1 ]
[ 616882-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	With Isopropyl acetate; tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Davies, Ian W. [Organic Letters, 2003, vol. 5, # 21, p. 3975 - 3978]

4
[ 139549-06-7 ]
[ 615552-65-3 ]
[ 796854-51-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrabutyl ammonium fluoride In Isopropyl acetate for 0.5h;
89%	With tetrabutyl ammonium fluoride In Isopropyl acetate for 0.5h;	3 EXAMLE 3; 2-[5-(4-methanesulfonyl-piperazin-1-ylmethyl)-2-nitro-phenyl]-1-(2-methoxy-quinolin-3-yl)-ethanol (5); To a mixture of 5.03 g (13.0 mmol) of 3 and 2.44 g (13.0 mmol) of 4 in 60 ML of isopropyl acetate was added dropwise 3.3 ML (3.25 mmol) of a 1 M solution of TBAF. After 30 min the reaction mixture was diluted with 35 mL of isopropyl acetate and washed with 50 mL of sat. NH4CL and 50 mL of water. The organic layer was dried over MGS04 and concentrated under reduced pressure to give 5.80 g (89%) of 5 as a colorless foam which was used in the next step without further purification. An analytical sample was obtained by chromatography on silica gel: 'H NMR (CDCL3, 400 MHz) 8 2.35 (M, 4H), 2.75 (s, 3H), 3.06 (M, 5H), 3.50 (M, 4H), 5.28 (t, 1H, J = 6.0 Hz), 7.11 (s, 1H), 7.29 (dd, 1H, J = 8.3 and 1.8 Hz), 7.38 (M, 1H), 7.60 (M, 1H), 7. 83 (d, 1H, J = 8.3 Hz), 7.90 (d, 1H, J = 8.4 Hz), 7.96 (s, 1H) ; 13C NMR (CDC13, 100 MHz) 8 34.3, 40.4, 45.8, 52.2, 53.6, 61.5, 70.3, 124.5, 125.0, 125.2, 126.9, 127.2, 127.5, 127.8, 129.6, 133.2, 133.4, 135.1, 143.3, 145.8, 149.2, 159.4 ; Anal. Calcd. For C24H28N406S L/2H2O : C, 56.57 ; H, 5.74 ; N, 10.99. Found: C, 56.65 ; H, 5.44 ; N, 10.83.
	With tetrabutyl ammonium fluoride In Isopropyl acetate for 0.5h;

Reference： [1]Wong, Audrey; Kuethe, Jeffrey T.; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7761 - 7764]
[2]Current Patent Assignee: MERCK & CO INC - WO2005/804, 2005, A2 Location in patent: Page/Page column 16
[3]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

5
[ 139549-06-7 ]
[ 796854-76-7 ]
[ 796854-70-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrabutyl ammonium fluoride In Isopropyl acetate at 20℃; for 0.5h;
74%	With tetrabutyl ammonium fluoride In tetrahydrofuran; Isopropyl acetate at 20℃; for 0.5h;

Reference： [1]Wong, Audrey; Kuethe, Jeffrey T.; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7761 - 7764]
[2]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

6
[ 139549-06-7 ]
[ 629643-43-2 ]
[ 629643-44-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetrabutyl ammonium fluoride In tetrahydrofuran; Isopropyl acetate at 20℃; for 0.5h;

Reference： [1]Wong, Audrey; Kuethe, Jeffrey T.; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7761 - 7764]

7
[ 67-56-1 ]
[ 73568-25-9 ]
[ 139549-06-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With C₇₂H₅₆N₁₆O₄Pd₄S₄; potassium hydroxide; phenylboronic acid for 8h; Reflux;
90.2%	With potassium carbonate In N,N-dimethyl-formamide for 6h; Reflux;	2.2.3. Synthesis of 2-Methoxyquinoline-3-carbaldehyde (5). A 100mL two-neck round-bottom Bask was charged withmethanol (10 mL), N,N-dimethylformamide (10 mL), 2-chloroquinoline-3-carbaldehyde (0.5 g, 0.0026 mol), andpotassium carbonate (0.67 g, 0.0048 mol); the mixture wasreBuxed using water condenser for 6 hours; and the progressof reaction was monitored with TLC. After completion of thereaction, methanol was removed by distillation, allowed tocool to room temperature, and then added to 100mL icecoldwater. +e solid product was collected by fractionaldistillation and washed with excess ice-cold water. +eamount of product was 0.44 g. Gray powder; yield 90.2%; mp106-108°C; Rf 0.32 (n-hexane:EtOAc 9 : 1; UV-Vis +max(MeOH) 295 nm; IR( cm-1, KBr): 3065.4 (aromatic C-Hstr.), 2919.3 (aliphatic C-H str.), 2847 (aliphatic C-H str.),1673 (aldehyde CO str.), 1620 (quinoline CN str.), 1599and 1579 (aromatic CC str.); 1H NMR (400 MHz, CDCl3),δH 4.22 (3H, s, H-10), 7.45 (1H, t, J 7.3 Hz, H-7), 7.76 (1H, t,J 7.7 Hz, H-6), 7.85 (2H, m, H-5, H-8), 8.60 (1H, s, H-4), and10.49 (1H, s, H-9); 13C NMR (100 MHz, CDCl3) ,δC 55.9 (C-10), 120.0 (C-3), 124.4 (C-6), 125.1 (C-4a), 127.1 (C-8), 129.8(C-5), 132.6 (C-7), 140.0 (C-3), 149.0 C-8a), 161.2 (C-2), and189.4 (C-9).
89%	With potassium hydroxide for 2.5h; Heating;

89%	With potassium hydroxide for 10h; Reflux;
89%	With potassium hydroxide at 60℃;	1.1 General procedure for the synthesis of 2-methoxyquinoline-3-carbaldehydes (19-24) To a solution of KOH (75.7 mmol) in MeOH (100 mL) was added the corresponding 2-chloro-3-quinolinecarbaldehyde (52.2 mmol) with constant stirring. The mixture was heated under reflux for 2.5-6 h and then cooled to room temperature. The product was precipitated out by adding water (300 mL) and then collected by vacuum filtration. The dried crude was recrystalised in DCM to afford compounds in yields ranging from 42-89%. 2-Methoxyquinoline-3-carbaldehyde (19) Yellow solid. Yield = 89%; M.p.: 96-98 °C; 1H NMR (300 MHz, CDCl3): δH = 10.46 (1H, s, CHO), 8.57 (1H, s, H-4), 7.88 - 7.82 (2H, m, H-5, H-8), 7.75 - 7.70 (1H, m, H-6), 7.45 - 7.39 (1H, m, H-7), 4.18 (3H, s, OCH3); 13C NMR (75 MHz, CDCl3): δC = 189.3, 161.2, 149.0, 140.0, 132.5, 129.7, 127.3, 125.0, 124.4, 120.1, 53.8.
89%	With potassium hydroxide Reflux;
85%	With potassium hydroxide for 3h; Reflux;
85%	With potassium hydroxide for 2.5h; Heating;
80%	With potassium hydroxide for 2.5h; Heating / reflux;	2 EXAMPLE 2; Preparation of 2-Methoxy-quinoline-3-carboxaldehyde (4); To a solution of 5 g (75.7 mmol) of KOH in 100 ML OF MEOH was added 10 g (52.2 mmol) of 2-chloro-3-quinolinecarboxaldehyde. The mixture was heated to reflux for 2.5 h and then cooled to rt. To the solution was added 300 mL of water and the precipitated product collected by filtration to afford 7.82 g (80%) of 4 as a tan solid. An analytical sample could be prepared by recrystallization from CH2CL2/HEXANES : mp 92-93 °C ; 'H NMR (CDCL3, 400 MHz) 8 4.14 (s, 3H), 7. 37 (dd, 1H, J = 8.0 and 6.9 Hz), 7.67 (M, 1H), 7.76 (d, 1H, J = 8.0 Hz), 7.80 (d, 1H, J = 8.4 HZ), 8.48 (s, 1H), 10.40 (s, 1H) ; 13C NMR (CDCL3, 100 MHz) 8 53.8, 120.0, 124.4, 125.0, 127.3, 129.7, 132.5, 139.9, 148.9, 161.1, 189.2 ; Anal. Calcd. FOR CLLH9NO2 : C, 70.58 ; H, 4.85 ; N, 7.48. Found: C, 70.44 ; H, 4.70 ; N, 7.39.
70%	With sodium carbonate at 65℃; for 4h;	Typical experimental procedure: General procedure: To a stirred solution of substrate (1 mmol, arylhalide/olefinic halide) in suitable alcohol (MeOH/EtOH, 10 mL), sodiumcarbonate (1.06 g, 2 mol %) was added and the reaction mixture was refluxed(MeOH = 65 C/EtOH = 78 C) for specified time. On completion, the reactionmixture was filtered, washed with methanol and dried in vacuo. The residuewas taken in ethyl acetate (20 mL) and washed with water. Organic layer wasdried over anhydrous sodium sulfate and evaporated in vacuo. The residuethus obtained was purified through Flash chromatography using ethyl acetate-hexane system. All the compounds were characterized and confirmed bycomparison of their spectral data and physical properties with reportedliterature
57%	With potassium hydroxide at 100 - 110℃; for 3h;	General procedure for the synthesis of 6-substituted-2-methoxyquinoline-3-carbaldehydes 3a-d General procedure: To a solutionof potassium hydroxide (1 g, 0.00178 mol) in 50 mL ofmethanol was added 6-substituted-2-chloroquinoline-3-carbaldehydes 2a-d (0.0131 mol). The mixture washeated cautiously at 100-110 °C for 3 h. After completionof the reaction, the resulting mixture was then cooled andpoured onto 200 g of crushed ice. The solid productobtained was filtered, washed with water, dried and purifiedby column chromatography (Pet. ether/Ethyl acetate 8:2).
	With potassium hydroxide Reflux;
	With potassium hydroxide Reflux;
	With sodium methylate at 60 - 70℃;
	With potassium carbonate for 6h; Reflux;
	With potassium hydroxide Reflux;	2-Methoxy-3-formylquinolines (1c and 1d). General procedure: A modified method of Waghray et al.40 was used. Briefly, the 2-chloro-3-formylquinolines 1a (10.4 mmol) and 1b (10.4 mmol) were added to a solution of potassiumhydroxide (15.6 mmol) in methanol (100 mL) and the contents refluxed overnight. Upon completion, thereaction was cooled to room temperature and cold water added to precipitate the product, which was thenfiltered and dried.
	With sodium at 40℃;	5.1.3 General procedure for preparation of 2-methoxyquinoline-3-carbaldehydes (4a-i) General procedure: To solution of sodium metal (0.05g, 2mmol) in methanol (10mL) a suspension of 2-chloroquinoline-3-carbaldehydes 3a-i (1mmol) in methanol (10mL) was added within 10min. The mixture was stirred at 40°C for 3-6h, then the reaction left to cool, neutralized with few drops of acetic acid and then poured onto ice H2O. The products were dried and crystallized using ethyl acetate [54-60].
	With potassium hydroxide at 100℃;	General procedure for the synthesis of N’-substituted-2-chloroquinoline-3-carbaldehydes2(a-e) and N’-substituted-2-methoxyquinoline-3-carbaldehydes 5(a-e) General procedure: Dimethylformamide 9.6 mL (0.125 mol) was takenin round bottom flask equipped with drying tube and phosphorus oxychloride 32.2 mL (0.35 mol) was added drop wise with continuous stirring at 0°C. To above solution different aryl acetanilide 1(a-e) (0.05 mol) were added and after 5 min the solution is heated under reflux for 16-17 h. The completion of the reaction was monitored by TLC, reaction contents were decanted into crushed ice with constant stirring. The settled solid was sieved, washed with water, dried and purified by recrystallization using ethyl acetate to afford final pure product 2(a-e) in good yield. Thus, obtained 2(a-e) (0.0131 mol) were refluxed at 100°C in a mixture containing 1 g of KOH (0.00178 mol) in 50 mL dried methanol for 2.5-3 h and then cooled to room temperature and decanted on crushed ice. The precipitated solid was sieved, washed with water, dried and purified by recrystallization from petroleum ether at 450 C.

Reference： [1]Nandhini, Sundar; Dharani, Sivadasan; Elamathi, Chennakrishnan; Dallemer, Frederic; Prabhakaran, Rathinasabapathi [Applied Organometallic Chemistry, 2021, vol. 35, # 12]
[2]Belay, Zerihun; Eswaramoorthy, Rajalakshmanan; Melaku, Yadessa; Zeleke, Digafie [Journal of Chemistry, 2020, vol. 2020]
[3]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[4]Waghray, Deepali; Zhang, Jing; Jacobs, Jeroen; Nulens, Wienand; Basaric, Nikola; Meervelt, Luc Van; Dehaen, Wim [Journal of Organic Chemistry, 2012, vol. 77, # 22, p. 10176 - 10183]
[5]Bokosi, Fostino R.B.; Beteck, Richard M.; Mbaba, Mziyanda; Mtshare, Thanduxolo E.; Laming, Dustin; Hoppe, Heinrich C.; Khanye, Setshaba D. [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 38]
[6]Bokosi, Fostino R. B.; Beteck, Richard M.; Jordaan, Audrey; Seldon, Ronnet; Warner, Digby F.; Tshiwawa, Tendamudzimu; Lobb, Kevin; Khanye, Setshaba D. [Journal of Heterocyclic Chemistry, 2021, vol. 58, # 11, p. 2140 - 2151]
[7]Location in patent: scheme or table Rajakumar, Perumal; Raja, Rathinam [Tetrahedron Letters, 2010, vol. 51, # 33, p. 4365 - 4370]
[8]Şişman, İlkay; Arslan, Barış Seçkin; Derin, Yavuz; Mısır, Büşra Albayrak; Nebioğlu, Mehmet; Tutar, Ahmet [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 12, p. 1542 - 1547][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 12, p. 1542 - 1547,6]
[9]Current Patent Assignee: MERCK & CO INC - WO2005/804, 2005, A2 Location in patent: Page/Page column 16
[10]Kumar, Balagani Sathish; Negi, Arvind S. [Tetrahedron Letters, 2015, vol. 56, # 18, p. 2340 - 2344]
[11]Joshi, Shrinivas D.; More, Uttam A.; Parkale, Deepak; Aminabhavi, Tejraj M.; Gadad, Andanappa K.; Nadagouda, Mallikarjuna N.; Jawarkar, Rahul [Medicinal Chemistry Research, 2015, vol. 24, # 11, p. 3892 - 3911]
[12]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 22, p. 6097 - 6105]
[13]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Anantram, Aarti; Seervi, Madhav; Sathaye, Sadhana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 645 - 649]
[14]Abdelbaset, Mahmoud S.; Abdel-Aziz, Mohamed; Abuo-Rahma, Gamal El-Din A.; Abdelrahman, Mostafa H.; Ramadan, Mohamed; Youssif, Bahaa G. M. [Archiv der Pharmazie, 2019, vol. 352, # 1]
[15]Thangaraj, Muthu; Ranjan, Bibhuti; Muthusamy, Ramesh; Murugesan, Arul; Gengan, Robert Moonsamy [Journal of Heterocyclic Chemistry, 2019, vol. 56, # 3, p. 867 - 885]
[16]Thungatha, Lamla; Alapour, Saba; Koorbanally, Neil A. [Arkivoc, 2020, vol. 2020, # 3, p. 74 - 89]
[17]Ibrahim, Tarek S.; Hawwas, Mohamed M.; Taher, Ehab S.; Alhakamy, Nabil A.; Alfaleh, Mohamed A.; Elagawany, Mohamed; Elgendy, Bahaa; Zayed, Gamal M.; Mohamed, Mamdouh F.A.; Abdel-Samii, Zakaria K.; Elshaier, Yaseen A.M.M. [Bioorganic Chemistry, 2020, vol. 105]
[18]Almehizia, Abdulrahman A.; Alshabi, Ali Mohamed; Joshi, Shrinivas D.; Kulkarni, Venkatarao H.; Kumar, R. Prem; Shaikh, Ibrahim Ahmed [Indian Journal of Heterocyclic Chemistry, 2021, vol. 31, # 1, p. 91 - 100]

8
[ 1779-49-3 ]
[ 139549-06-7 ]
[ 850171-39-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-methoxy-3-quinolinecarboxyaldehyde In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

9
[ 851777-21-4 ]
2-(2-methoxy-quinolin-3-yl)-2,3-dihydro-benzofuran-5-carboxylic acid methyl ester [ No CAS ]
[ 139549-06-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 20%	With tetrabutyl ammonium fluoride at 20℃;

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Journet, Michel; Davies, Ian W. [Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3727 - 3729]

10
[ 96784-54-2 ]
[ 139549-06-7 ]
3-(5-cyano-2,3-dihydro-1-benzofuran-2-yl)-2-methoxyquinoline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 3727 - 3729

11
[ 5367-28-2 ]
[ 139549-06-7 ]
[ 861631-59-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide for 3h;

Reference： [1]Davies, Ian W.; Smitrovich, Jacqueline H.; Sidler, Rick; Qu, Chuanxing; Gresham, Venita; Bazaral, Charles [Tetrahedron, 2005, vol. 61, # 26, p. 6425 - 6437]

12
[ 24078-21-5 ]
[ 139549-06-7 ]
[ 851777-21-4 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 6425 - 6437

13
[ 24078-21-5 ]
[ 139549-06-7 ]
2-(2-methoxy-quinolin-3-yl)-2,3-dihydro-benzofuran-5-carboxylic acid methyl ester [ No CAS ]
[ 3113-71-1 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 3727 - 3729

14
[ 103368-91-8 ]
[ 139549-06-7 ]
2-(2-methoxy-quinolin-3-yl)-2,3-dihydro-benzofuran-5-carboxylic acid methyl ester [ No CAS ]
[ 851777-21-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Journet, Michel; Davies, Ian W. [Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3727 - 3729]

15
[ 139549-06-7 ]
3-(5-chloro-1H-indol-2-yl)-2-methoxyquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 84 percent / DBU / dimethylsulfoxide / 3 h 2: 93 percent / trifluoroacetic anhydride; DBU / isopropyl acetate / 14 h 3: 91 percent / CO; 1,10-phenanthroline / palladium(II) acetate / dimethylformamide / 16 h / 80 °C / 775.72 Torr

Reference： [1]Davies, Ian W.; Smitrovich, Jacqueline H.; Sidler, Rick; Qu, Chuanxing; Gresham, Venita; Bazaral, Charles [Tetrahedron, 2005, vol. 61, # 26, p. 6425 - 6437]

16
[ 139549-06-7 ]
[ 861631-69-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 80 percent / DBU / dimethylsulfoxide / 3 h 2: 87 percent / trifluoroacetic anhydride; DBU / isopropyl acetate / 14 h 3: 78 percent / 3,4,7,8-tetramethyl-1,10-phenanthroline; CO / palladium(II) trifluoroacetate / dimethylformamide / 16 h / 80 °C / 775.72 Torr

Reference： [1]Davies, Ian W.; Smitrovich, Jacqueline H.; Sidler, Rick; Qu, Chuanxing; Gresham, Venita; Bazaral, Charles [Tetrahedron, 2005, vol. 61, # 26, p. 6425 - 6437]

17
[ 139549-06-7 ]
cis-3-{2-[5-(4-methanesulfonylpiperazin-1-ylmethyl)-2-nitrophenyl]vinyl}-2-methoxyquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrabutylammonium fluoride / isopropyl acetate / 0.5 h 2.1: CF₃CO₂H / isopropyl acetate / 0.5 h / 20 °C 2.2: 80 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl acetate / 0.5 h / 60 °C 3.1: 40 percent / dimethylformamide / 16 h / UV-irradiation
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C 1.2: 81 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 63 percent / P(o-tolyl)3; Et₃N; Pd(OAc)2 / dimethylformamide / 4 h / 100 °C 3.1: 40 percent / dimethylformamide / 16 h / UV-irradiation

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[2]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

18
[ 139549-06-7 ]
[ 820976-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrabutylammonium fluoride / isopropyl acetate / 0.5 h 2.1: CF₃CO₂H / isopropyl acetate / 0.5 h / 20 °C 2.2: 80 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl acetate / 0.5 h / 60 °C
	Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C 1.2: 81 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 63 percent / P(o-tolyl)3; Et₃N; Pd(OAc)2 / dimethylformamide / 4 h / 100 °C

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[2]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

19
[ 139549-06-7 ]
3-(5-[4-(4-methanesulfonyl)-1-piperazinyl]methyl}-1H-indol-2-yl)quinolin-2(1H)-one hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tetrabutylammonium fluoride / isopropyl acetate / 0.5 h 2.1: CF₃CO₂H / isopropyl acetate / 0.5 h / 20 °C 2.2: 80 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl acetate / 0.5 h / 60 °C 3.1: 95 percent / PPh₃; CO / Pd(OAc)2 / acetonitrile / 15 h / 70 °C / 3102.89 Torr 4.1: 100 percent / HCl / dimethylformamide; H₂O / 2 h / 70 °C
	Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C 1.2: 81 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 63 percent / P(o-tolyl)3; Et₃N; Pd(OAc)2 / dimethylformamide / 4 h / 100 °C 3.1: 95 percent / PPh₃; CO / Pd(OAc)2 / acetonitrile / 15 h / 70 °C / 3102.89 Torr 4.1: 100 percent / HCl / dimethylformamide; H₂O / 2 h / 70 °C

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[2]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

20
[ 139549-06-7 ]
2,2'-bis(2-methoxyquinolin-3-yl)-5,5'--(methylsulfonyl)piperazin-1-yl]methyl}-1H,1'H-3,3'-biindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrabutylammonium fluoride / isopropyl acetate / 0.5 h 2.1: CF₃CO₂H / isopropyl acetate / 0.5 h / 20 °C 2.2: 80 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl acetate / 0.5 h / 60 °C 3.1: PPh₃; CO / Pd(OAc)2 / acetonitrile / 15 h / 70 °C / 3102.89 Torr
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C 1.2: 81 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 63 percent / P(o-tolyl)3; Et₃N; Pd(OAc)2 / dimethylformamide / 4 h / 100 °C 3.1: PPh₃; CO / Pd(OAc)2 / acetonitrile / 15 h / 70 °C / 3102.89 Torr

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[2]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

21
[ 139549-06-7 ]
2-methoxy-3-(5-methyl-1H-indol-2-yl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 74 percent / TBAF / tetrahydrofuran; isopropyl acetate / 0.5 h / 20 °C 2: 69 percent / DMSO; Ac₂O / isopropyl acetate / 4 h / 80 °C 3: 76 percent / H₂ / Raney nickel 2800 / tetrahydrofuran / 7.5 h / 65 °C / 2068.59 Torr
	Multi-step reaction with 3 steps 1: 74 percent / TBAF / isopropyl acetate / 0.5 h / 20 °C 2: 69 percent / DMSO; acetic anhydride / isopropyl acetate / 4 h / 80 °C 3: 76 percent / H₂ / Raney Nickel 2800 (H₂O) / tetrahydrofuran / 7.5 h / 65 °C / 2068.59 Torr

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[2]Wong, Audrey; Kuethe, Jeffrey T.; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7761 - 7764]

22
[ 139549-06-7 ]
2-(2-amino-5-methylphenyl)-1-(2-methoxyquinolin-3-yl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 74 percent / TBAF / tetrahydrofuran; isopropyl acetate / 0.5 h / 20 °C 2: 58 percent / H₂ / Raney nickel 2800 / tetrahydrofuran / 6 h / 65 °C / 2068.59 Torr
	Multi-step reaction with 2 steps 1: 74 percent / TBAF / isopropyl acetate / 0.5 h / 20 °C 2: 58 percent / H₂ / Raney Nickel 2800 (H₂O) / tetrahydrofuran / 6 h / 65 °C / 2068.59 Torr

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[2]Wong, Audrey; Kuethe, Jeffrey T.; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7761 - 7764]

23
[ 139549-06-7 ]
[ 796854-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 74 percent / TBAF / tetrahydrofuran; isopropyl acetate / 0.5 h / 20 °C 2: 69 percent / DMSO; Ac₂O / isopropyl acetate / 4 h / 80 °C
	Multi-step reaction with 2 steps 1: 74 percent / TBAF / isopropyl acetate / 0.5 h / 20 °C 2: 69 percent / DMSO; acetic anhydride / isopropyl acetate / 4 h / 80 °C

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[2]Wong, Audrey; Kuethe, Jeffrey T.; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7761 - 7764]

24
[ 139549-06-7 ]
[ 796854-61-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrabutylammonium fluoride / isopropyl acetate / 0.5 h 2.1: CF₃CO₂H / isopropyl acetate / 0.5 h / 20 °C 2.2: 80 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl acetate / 0.5 h / 60 °C 3.1: 95 percent / PPh₃; CO / Pd(OAc)2 / acetonitrile / 15 h / 70 °C / 3102.89 Torr
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C 1.2: 81 percent / tetrahydrofuran / 1 h / 20 °C 2.1: 63 percent / P(o-tolyl)3; Et₃N; Pd(OAc)2 / dimethylformamide / 4 h / 100 °C 3.1: 95 percent / PPh₃; CO / Pd(OAc)2 / acetonitrile / 15 h / 70 °C / 3102.89 Torr

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]
[2]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

25
[ 139549-06-7 ]
2-(2-amino-5-[4-(methylsulfonyl)piperazin-1-yl]methyl}phenyl)-1-(2-methoxyquinolin-3-yl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammonium fluoride / isopropyl acetate / 0.5 h 2: 86 percent / H₂ / Raney nickel 2800 / tetrahydrofuran / 6 h / 65 °C / 2068.59 Torr

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

26
[ 139549-06-7 ]
2-chloro-1-(2-methoxyquinolin-3-yl)-2-(5-[4-(methanesulfonyl)piperazin-1-yl]methyl}-2-nitrophenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammonium fluoride / isopropyl acetate / 0.5 h 2: 47 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -65 - 20 °C

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

27
[ 139549-06-7 ]
1-(2-methoxyquinolin-3-yl)-2-(5-[4-(methylsulfonyl)piperazin-1-yl]methyl}-2-nitrophenyl)ethyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammonium fluoride / isopropyl acetate / 0.5 h 2: 65 percent / isopropyl acetate / 80 °C

Reference： [1]Kuethe, Jeffrey T.; Wong, Audrey; Qu, Chuanxing; Smitrovich, Jacqueline; Davies, Ian W.; Hughes, David L. [Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2555 - 2567]

28
[ 139549-06-7 ]
5-ethyl-6-hydroxymethyl-3-{N-[(2-methoxyquinolin-3-yl)methyl]amino}pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		30 Preparation of 5-Ethyl-6-hydroxymethyl-3-{N-[(2-methoxyquinolin-3-yl)methyl]amino}pyridin-2(1H)-one EXAMPLE 30 Preparation of 5-Ethyl-6-hydroxymethyl-3-{N-[(2-methoxyquinolin-3-yl)methyl]amino}pyridin-2(1H)-one Following the procedures of Example 11 and starting with 2-methoxyquinoline-3-carboxaldehyde, the title compound is obtained.

Reference： [1]Current Patent Assignee: MERCK & CO INC - EP481802, 1992, A1

29
[ 139549-06-7 ]
[ 1038969-22-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With methanol; sodium tetrahydroborate at 0℃;	(2-methoxyquinolin-3-yl)methanol (2-methoxyquinolin-3-yl)methanol 2-Methoxyquinoline-3-carbaldehyde (1.45 g, 7.75 mmol) was suspended in methanol (20 mL) and the mixture was cooled to 0° C. Sodium borohydride (600 mg, 15.86 mmol) was added, causing bubbling. The reaction mixture was stirred and gradually warmed to room temperature overnight (let ice bath melt). The reaction mixture was concentrated, and the crude material was taken up in saturated aqueous bicarbonate solution (50 mL) and extracted with dichloromethane (2*50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford the title compound (1.46 g, 7.72 mmol, 100% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.19 (q, J=1.2 Hz, 1H), 7.90 (dd, J=8.0, 1.5 Hz, 1H), 7.82-7.72 (m, 1H), 7.62 (ddd, J=8.4, 6.9, 1.5 Hz, 1H), 7.42 (ddd, J=8.1, 6.9, 1.2 Hz, 1H), 5.44-5.30 (m, 1H), 4.66-4.54 (m, 2H), 4.01 (s, 3H); MS (ESI+) m/z 190 (M+H)+.
93%	With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃;
87%	With sodium tetrahydroborate In methanol at 0 - 20℃; for 6h;

Reference： [1]Current Patent Assignee: ABBVIE INC; GALAPAGOS - US2018/99932, 2018, A1 Location in patent: Paragraph 1511; 1521; 1798
[2]Waghray, Deepali; Zhang, Jing; Jacobs, Jeroen; Nulens, Wienand; Basaric, Nikola; Meervelt, Luc Van; Dehaen, Wim [Journal of Organic Chemistry, 2012, vol. 77, # 22, p. 10176 - 10183]
[3]Location in patent: scheme or table Rajakumar, Perumal; Raja, Rathinam [Tetrahedron Letters, 2010, vol. 51, # 33, p. 4365 - 4370]

30
[ 1250257-48-7 ]
[ 139549-06-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydrogenchloride In tetrahydrofuran at 80℃; for 1h;

Reference： [1]Location in patent: experimental part Rajeev; Rajendran [Synthetic Communications, 2010, vol. 40, # 19, p. 2837 - 2843]

31
[ 623-33-6 ]
[ 139549-06-7 ]
[ 1250257-55-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: glycine ethyl ester hydrochloride With triethylamine In benzene at 20℃; Stage #2: 2-methoxy-3-quinolinecarboxyaldehyde In benzene at 20℃;

Reference： [1]Location in patent: experimental part Rajeev; Rajendran [Synthetic Communications, 2010, vol. 40, # 19, p. 2837 - 2843]

32
[ 118-93-4 ]
[ 139549-06-7 ]
[ 1329423-64-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With barium dihydroxide In methanol at 40℃; for 24h;

Reference： [1]Location in patent: scheme or table Bouraioua, Abelmalek; Berreeb, Fabienne; Bouacidac, Sofiane; Carbonib, Bertrand; Debachea, Abdelmadjid; Royneld, Thierry; Belfaitah, Ali [Letters in Organic Chemistry, 2011, vol. 8, # 6, p. 374 - 379]

33
[ 1407185-49-2 ]
[ 139549-06-7 ]
[ 1407185-54-9 ]
[ 1407185-55-0 ]

Yield	Reaction Conditions	Operation in experiment
50 % de	With sodium hydride In dichloromethane at 0 - 20℃; for 6h; Overall yield = 82 %; Overall yield = 0.75 g;

Reference： [1]Waghray, Deepali; Zhang, Jing; Jacobs, Jeroen; Nulens, Wienand; Basaric, Nikola; Meervelt, Luc Van; Dehaen, Wim [Journal of Organic Chemistry, 2012, vol. 77, # 22, p. 10176 - 10183]

34
[ 67-56-1 ]
[ 73568-25-9 ]
[ 70659-29-9 ]
[ 1038969-22-0 ]
[ 139549-06-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 6% 3: 21%	With potassium hydroxide at 20℃; for 24h;

Reference： [1]Kumar, Devadoss Karthik; Shankar, Rajakandhan; Rajendran, Subramaniam Parameswaran [Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1071 - 1076]

35
[ 139549-06-7 ]
[ 67-64-1 ]
4-(2-methoxyquinolin-3-yl)but-3-en-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sulfuric acid for 6h; Reflux;

Reference： [1]Kumar, Devadoss Karthik; Shankar, Rajakandhan; Rajendran, Subramaniam Parameswaran [Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1071 - 1076]

36
[ 104-86-9 ]
[ 139549-06-7 ]
C₁₈H₁₅ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In ethanol Reflux;	Synthesis of N-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine (8c) General procedure: Compound 6 (1.5 g, 8.0mmol) was dissolved in ethanol (20 mL) containing catalytic amount of glacialacetic acid (45 μL, 0.8mmol). 4-methoxybenzylamine (7c, 1.1 mL, 8.4mmol) was added drop wise.Reaction mixture was heated at reflux overnight, cooled and sodium borohydride (0.6 g, 16.0mmol) wasadded in small portions. After the effervescence ceased, the reaction was stirred at room temperature for6 h. Water (50 mL) was added and ethanol was evaporated on vacuum evaporator. The aqueous solutionwas extracted with 2 x 20 mL portions of dichloromethane. The combined organic layers were washedwith brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The crudeproduct was purified by column chromatography (silica gel, Hexane/EtOAc, gradient elution), to obtainN-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine (8c, 2.0 g, 81.0%) as amber coloredsolid; m.p.: 95-97 °C; IR (KBr): Vmax cm-1 3313

Reference： [1]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 22, p. 6097 - 6105]

37
[ 103-84-4 ]
[ 139549-06-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 16.5 h / 80 °C 2: potassium hydroxide / Reflux
	Multi-step reaction with 2 steps 1: trichlorophosphate / 0 °C / Reflux 2: potassium hydroxide / 3 h / 100 - 110 °C
	Multi-step reaction with 2 steps 1: trichlorophosphate / 16.5 h / 80 °C 2: potassium hydroxide / Reflux

	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0 - 5 °C 1.2: 80 - 90 °C 2.1: potassium carbonate / 6 h / Reflux
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / -5 °C / Inert atmosphere 1.2: 80 °C / Inert atmosphere 2.1: methanol / 70 °C
	Multi-step reaction with 2 steps 1: trichlorophosphate / 18 h / 70 °C 2: ethanol / 40 °C
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.5 h / 0 °C 1.2: 22 h / 85 - 90 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / Reflux
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.33 h / 0 - 5 °C 1.2: 18 h / 80 - 90 °C 2.1: potassium hydroxide / Reflux
	Multi-step reaction with 2 steps 1: trichlorophosphate / 18 h / 0 - 90 °C 2: sodium / 40 °C
	Multi-step reaction with 2 steps 1: trichlorophosphate / 18 h / 70 - 90 °C 2: methanol / 40 °C
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0 °C 1.2: 16 h / Heating 2.1: potassium hydroxide / 2.5 h / Heating
	Multi-step reaction with 2 steps 1: trichlorophosphate / 18 h / 70 - 90 °C 2: methanol / 40 °C
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 1 h / 0 - 5 °C 1.2: 0 - 80 °C / Inert atmosphere 2.1: potassium hydroxide / 60 °C
	Multi-step reaction with 2 steps 1: trichlorophosphate / 0 °C / Reflux; Heating 2: potassium hydroxide / 100 °C
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 1 h / 0 - 5 °C / Inert atmosphere 1.2: 0 °C / Inert atmosphere; Reflux 2.1: potassium hydroxide / Reflux

Reference： [1]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 22, p. 6097 - 6105]
[2]Joshi, Shrinivas D.; More, Uttam A.; Parkale, Deepak; Aminabhavi, Tejraj M.; Gadad, Andanappa K.; Nadagouda, Mallikarjuna N.; Jawarkar, Rahul [Medicinal Chemistry Research, 2015, vol. 24, # 11, p. 3892 - 3911]
[3]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Anantram, Aarti; Seervi, Madhav; Sathaye, Sadhana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 645 - 649]
[4]Thangaraj, Muthu; Ranjan, Bibhuti; Muthusamy, Ramesh; Murugesan, Arul; Gengan, Robert Moonsamy [Journal of Heterocyclic Chemistry, 2019, vol. 56, # 3, p. 867 - 885]
[5]Karkara, Bidhu Bhusan; Mishra, Shashank Shekhar; Panda, Gautam; Singh, Bhupendra N. [Bioorganic Chemistry, 2020, vol. 99]
[6]AL-Mahmoudy, Amany M. M.; Abdel-Aal, Eatedal H.; AlAwadh, Mohammed A.; Alhakamy, Nabil A.; Asfour, Hany Z.; Bokhtia, Riham M.; Elagawany, Mohamed; Gouda, Ahmed M.; Ibrahim, Tarek S.; Panda, Siva; Taher, Ehab S.; Youssif, Bahaa G. M. [Bioorganic Chemistry, 2020, vol. 99]
[7]Belay, Zerihun; Eswaramoorthy, Rajalakshmanan; Melaku, Yadessa; Zeleke, Digafie [Journal of Chemistry, 2020, vol. 2020]
[8]Thungatha, Lamla; Alapour, Saba; Koorbanally, Neil A. [Arkivoc, 2020, vol. 2020, # 3, p. 74 - 89]
[9]Ibrahim, Tarek S.; Hawwas, Mohamed M.; Taher, Ehab S.; Alhakamy, Nabil A.; Alfaleh, Mohamed A.; Elagawany, Mohamed; Elgendy, Bahaa; Zayed, Gamal M.; Mohamed, Mamdouh F.A.; Abdel-Samii, Zakaria K.; Elshaier, Yaseen A.M.M. [Bioorganic Chemistry, 2020, vol. 105]
[10]Ibrahim, Tarek S.; Hawwas, Mohamed M.; Malebari, Azizah M.; Taher, Ehab S.; Omar, Abdelsattar M.; O’boyle, Niamh M.; McLoughlin, Eavan; Abdel-Samii, Zakaria K.; Elshaier, Yaseen A. M. M. [Pharmaceuticals, 2020, vol. 13, # 11, p. 1 - 22] Ibrahim, Tarek S.; Hawwas, Mohamed M.; Malebari, Azizah M.; Taher, Ehab S.; Omar, Abdelsattar M.; Neamatallah, Thikryat; Abdel-Samii, Zakaria K.; Safo, Martin K.; Elshaier, Yaseen A. M. M. [Journal of Enzyme Inhibition and Medicinal Chemistry, 2021, vol. 36, # 1, p. 802 - 818]
[11]Şişman, İlkay; Arslan, Barış Seçkin; Derin, Yavuz; Mısır, Büşra Albayrak; Nebioğlu, Mehmet; Tutar, Ahmet [Chemistry of Heterocyclic Compounds, 2020, vol. 56, # 12, p. 1542 - 1547][Khim. Geterotsikl. Soedin., 2020, vol. 56, # 12, p. 1542 - 1547,6]
[12]Current Patent Assignee: KING ABDULAZIZ UNIVERSITY - US10882852, 2021, B1
[13]Bokosi, Fostino R.B.; Beteck, Richard M.; Mbaba, Mziyanda; Mtshare, Thanduxolo E.; Laming, Dustin; Hoppe, Heinrich C.; Khanye, Setshaba D. [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 38]
[14]Almehizia, Abdulrahman A.; Alshabi, Ali Mohamed; Joshi, Shrinivas D.; Kulkarni, Venkatarao H.; Kumar, R. Prem; Shaikh, Ibrahim Ahmed [Indian Journal of Heterocyclic Chemistry, 2021, vol. 31, # 1, p. 91 - 100]
[15]Bokosi, Fostino R. B.; Beteck, Richard M.; Jordaan, Audrey; Seldon, Ronnet; Warner, Digby F.; Tshiwawa, Tendamudzimu; Lobb, Kevin; Khanye, Setshaba D. [Journal of Heterocyclic Chemistry, 2021, vol. 58, # 11, p. 2140 - 2151]

38
[ 139549-06-7 ]
[ 100-46-9 ]
C₁₈H₁₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In ethanol Reflux;	Synthesis of N-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine (8c) General procedure: Compound 6 (1.5 g, 8.0mmol) was dissolved in ethanol (20 mL) containing catalytic amount of glacialacetic acid (45 μL, 0.8mmol). 4-methoxybenzylamine (7c, 1.1 mL, 8.4mmol) was added drop wise.Reaction mixture was heated at reflux overnight, cooled and sodium borohydride (0.6 g, 16.0mmol) wasadded in small portions. After the effervescence ceased, the reaction was stirred at room temperature for6 h. Water (50 mL) was added and ethanol was evaporated on vacuum evaporator. The aqueous solutionwas extracted with 2 x 20 mL portions of dichloromethane. The combined organic layers were washedwith brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The crudeproduct was purified by column chromatography (silica gel, Hexane/EtOAc, gradient elution), to obtainN-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine (8c, 2.0 g, 81.0%) as amber coloredsolid; m.p.: 95-97 °C; IR (KBr): Vmax cm-1 3313

Reference： [1]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 22, p. 6097 - 6105]

39
[ 139549-06-7 ]
[ 104-84-7 ]
C₁₉H₁₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In ethanol Reflux;	Synthesis of N-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine (8c) General procedure: Compound 6 (1.5 g, 8.0mmol) was dissolved in ethanol (20 mL) containing catalytic amount of glacialacetic acid (45 μL, 0.8mmol). 4-methoxybenzylamine (7c, 1.1 mL, 8.4mmol) was added drop wise.Reaction mixture was heated at reflux overnight, cooled and sodium borohydride (0.6 g, 16.0mmol) wasadded in small portions. After the effervescence ceased, the reaction was stirred at room temperature for6 h. Water (50 mL) was added and ethanol was evaporated on vacuum evaporator. The aqueous solutionwas extracted with 2 x 20 mL portions of dichloromethane. The combined organic layers were washedwith brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The crudeproduct was purified by column chromatography (silica gel, Hexane/EtOAc, gradient elution), to obtainN-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine (8c, 2.0 g, 81.0%) as amber coloredsolid; m.p.: 95-97 °C; IR (KBr): Vmax cm-1 3313

Reference： [1]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 22, p. 6097 - 6105]

40
[ 2393-23-9 ]
[ 139549-06-7 ]
N-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In ethanol Reflux;	Synthesis of N-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine (8c) General procedure: Compound 6 (1.5 g, 8.0mmol) was dissolved in ethanol (20 mL) containing catalytic amount of glacialacetic acid (45 μL, 0.8mmol). 4-methoxybenzylamine (7c, 1.1 mL, 8.4mmol) was added drop wise.Reaction mixture was heated at reflux overnight, cooled and sodium borohydride (0.6 g, 16.0mmol) wasadded in small portions. After the effervescence ceased, the reaction was stirred at room temperature for6 h. Water (50 mL) was added and ethanol was evaporated on vacuum evaporator. The aqueous solutionwas extracted with 2 x 20 mL portions of dichloromethane. The combined organic layers were washedwith brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The crudeproduct was purified by column chromatography (silica gel, Hexane/EtOAc, gradient elution), to obtainN-(4-methoxybenzyl)-1-(2-methoxyquinolin-3-yl)methanamine (8c, 2.0 g, 81.0%) as amber coloredsolid; m.p.: 95-97 °C; IR (KBr): Vmax cm-1 3313

Reference： [1]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 22, p. 6097 - 6105]

41
[ 139549-06-7 ]
[ 292638-85-8 ]
methyl 2-[hydroxy(2-methoxyquinolin-3-yl)methyl]prop-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; chloroform at 0℃;	prepared from 2-methoxy-3-formylquinoleine and methyl acrylate from a general process [19,20] in pyridine and chloroform at low temperature (0 C)

Reference： [1]Djemel, Tarek; Messai, Amel; Luneau, Dominique; Jeanneau, Earwann [Journal of Chemical Crystallography, 2015, vol. 45, # 6, p. 300 - 309]

42
[ 54-85-3 ]
[ 139549-06-7 ]
N'-[(2-methoxyquinolin-3-yl)methylene]isonicotinohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With acetic acid In ethanol Reflux;	General procedure for the synthesis of N'-[(6-substituted-2-methoxyquinolin-3-yl) methylene]isonicotinohydrazides 4a-d General procedure: A mixture of 3a-d (0.005 mol) and isoniazid(0.005 mol) in ethanol (20 mL) was refluxed for 4-6 h inthe presence of few drops of glacial acetic acid. Thecompletion of reaction was detected by TLC. Solvent wasevaporated under reduced pressure and poured onto crushedice, and the resultant solid was recrystallized fromethanol and DMF mixture to give the products.

Reference： [1]Joshi, Shrinivas D.; More, Uttam A.; Parkale, Deepak; Aminabhavi, Tejraj M.; Gadad, Andanappa K.; Nadagouda, Mallikarjuna N.; Jawarkar, Rahul [Medicinal Chemistry Research, 2015, vol. 24, # 11, p. 3892 - 3911]

43
[ 139549-06-7 ]
[ 112575-84-5 ]
N'-[(2-methoxyquinolin-3-yl)methylene]-4-(1H-pyrrol-1-yl)benzohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With acetic acid In ethanol Reflux;	General procedure for synthesis of N'-[(6-substituted-2-methoxyquinolin-3-yl) methylene]-4-(1H-pyrrol-1-yl)benzohydrazides 5a-d General procedure: A mixture of 3a-d (0.005 mol) and4-(1H-pyrrol-1-yl)benzohydrazide (0.005 mol) (Joshiet al., 2008) in ethanol (20 mL) was refluxed for 4-6 h inthe presence of few drops of glacial acetic acid. Thecompletion of reaction was detected by TLC. Solvent wasevaporated under reduced pressure and poured onto crushedice, and the resultant solid was recrystallized fromethanol and DMF mixture to give the products.

Reference： [1]Joshi, Shrinivas D.; More, Uttam A.; Parkale, Deepak; Aminabhavi, Tejraj M.; Gadad, Andanappa K.; Nadagouda, Mallikarjuna N.; Jawarkar, Rahul [Medicinal Chemistry Research, 2015, vol. 24, # 11, p. 3892 - 3911]

44
[ 372-09-8 ]
[ 139549-06-7 ]
3-(2-methoxyquinolin-3-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.14%	With pyridine; ammonium acetate In toluene for 44h; Reflux; Dean-Stark;	Synthesis of 3-(2-methoxyquinolin-3-yl)acrylonitrile (7) A mixture of 2-methoxy-3-formylquinoline (6, 5.0g, 26.71 mmol), cyanoacetic acid (2.3g, 27.04 mmol), ammonium acetate (100mg, 1.3 mmol) and pyridine (15mL) was refluxed in 30 mL of toluene for 44 h in a flask fitted with a Dean-Stark apparatus and condenser. After evaporation of solvents, a solution of the residue in CH2Cl2 was washed with water, dried over sodium sulphate, and evaporated in vacuo. The crude product was purified by column chromatography (silica gel, Hexane/EtOAc, gradient elution) to give 4.5g of 3-(2-methoxyquinolin-3-yl)acrylonitrile (7) as cream colored solid

Reference： [1]Jain, Puneet P.; Degani, Mariam S.; Raju, Archana; Anantram, Aarti; Seervi, Madhav; Sathaye, Sadhana; Ray, Muktikanta; Rajan [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 645 - 649]

45
[ 59-48-3 ]
[ 139549-06-7 ]
(E)-3-((2-methoxyquinolin-3-yl)methylene)indolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyrrolidine In ethanol at 20℃; for 6h;

Reference： [1]Mathusalini, Sadasivam; Arasakumar, Thangaraj; Lakshmi, Krishnasamy; Lin, Chia-Her; Mohan, Palathurai Subramaniam; Ramnath, Madhusudhanan Gogul; Thirugnanasampandan, Ramaraj [New Journal of Chemistry, 2016, vol. 40, # 6, p. 5164 - 5169]

46
[ 139549-06-7 ]
[ 62-53-3 ]
[ 762-04-9 ]
diethyl ((2-methoxyquinolin-3-yl)(phenylamino)methyl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With cobalt supported on boron nitride In toluene for 3h; Reflux; Inert atmosphere;	3.3 Typical procedure for the synthesis α-amino quinolinephosphonates General procedure: In a 50 mL round bottom flask, aniline (1 mmol), 2-methoxy-3-formyl quinoline (1 mmol) and diethyl phosphite (1 mmol)were added to toluene (6 mL) followed by CoBNT (10 mol%). The reaction mixture was refluxed for 3 h under an inert atmosphere.The progress of the reaction was continuously monitored through TLC. After completion of the reaction, the solid catalyst was filtered and kept aside for re-use. The solvent in the reaction mixture was removed in vacuumand the solid productwas purified by column chromatography with an eluting solventsystem of petroleum ether and ethyl acetate (7:3) pure α-aminoquinoline phosphonate (4a) of yield 96% was obtained. This protocolwas used to optimize the model reaction and to synthesise15 other novel quinoline phosphonates. To investigate the recyclability of the catalyst, the filtered solid was rinsed with chloroformand methanol, air dried, and then used in the modelreaction.