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[ CAS No. 749920-54-5 ] {[proInfo.proName]}

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Chemical Structure| 749920-54-5
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CAS No. :749920-54-5 MDL No. :MFCD06337019
Formula : C10H5ClFNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :209.60 Pubchem ID :-
Synonyms :

Safety of [ 749920-54-5 ]

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

Application In Synthesis of [ 749920-54-5 ]

* 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.

  • Downstream synthetic route of [ 749920-54-5 ]

[ 749920-54-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 351-83-7 ]
  • [ 33513-42-7 ]
  • [ 749920-54-5 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; for 1h; Stage #2: N1-(4-Fluorophenyl)acetamide at 0 - 80℃; Inert atmosphere; 1.1 General procedure for synthesis of 2-chloroquinoline-3-carbaldehydes (13-18) General procedure: A round bottom flask charged with N, N-dimethylformamide (7.0 mol) was placed on an ice bath and the temperature kept at 0-5 °C. To this flask, phosphorus oxychloride (12.0 mol) was added dropwise and the reaction mixture was stirred for 1 h at 0-5 °C. The appropriate N-phenylacetamide (1.0 mol) was then added and stirred for a further 30 min followed by heating under reflux for 5-4 h under N2 atmosphere. After the reaction was completed (TLC monitoring), the mixture was poured into 200 g of crushed ice under constant stirring. The precipitate obtained was vacuum filtered, washed with water (2 × 30 mL), air-dried and recrystallised from EtOAc to give the relevant compounds in 36-84% yields.
55% Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: N1-(4-Fluorophenyl)acetamide at 0℃; Inert atmosphere; Reflux;
40% With trichlorophosphate at 85℃; for 24h;
15% With trichlorophosphate at 0 - 82℃; 36a; 36b 2-Chloro-6-fluoroquinoline-3-carbaldehyde To DMF (18.94 mL, 18.94 mL) at 0° C. was added POCl3 (63.90 mL, 685.6 mmol) dropwise, then N-(4-fluorophenyl)acetamide (15.00 g, 97.94 mmol) portionwise. The mixture was stirred at 0° C. for 20 min, then at 82° C. overnight. The mixture was allowed to cool to RT then poured into ice-water. Precipitate was collected by filtration and and dried to give the title compound as a yellow solid (3.16 g, 15%). MS (ES+): C10H5ClFNO requires: 209, found: 210 [M+H]+.
13% Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: N1-(4-Fluorophenyl)acetamide In dichloromethane at 85℃; for 19h; Inert atmosphere; 2-chloro-3-formyl-6-fluoroquinoline (10). Under anhydrous argon atmosphere, POCl3(4.2 mL, 45.7 mmol) was added dropwise to precooled (0 °C) anhydrous DMF (1.25 mL,16.3 mmol). The solution was allowed to warm to room temperature (15 min) and thentreated with compound 8 (1.00 g, 6.53 mmol). The round-bottom flask was sealed, and thesolution was stirred at 85 °C for 19 h. After cooling to room temperature, the solution wasthen poured over ice (100 mL). The yellow precipitate was filtered, washed with deionisedwater (20 mL), and dried under vacuum to provide compound 10 (182 mg, 0.868 mmol,13%) as a yellow powder. Rf (SiO2, cyclohexane/EtOAc, 9/1, v/v) 0.40. IR (ATR, cm-1) 1693(νC=O), 1581, 1497 (νC=C), 1337 (νC-N), 1220 (νC-F), 1046 (νS=O), 834 (δCH op). Mp 180 ± 1 °C. 1HNMR (500 MHz, CDCl3) δ 10.38 (s, 1H, CHO), 8.97 (s, 1H, H-4), 8.15-8.10 (m, 2H, H-5, H-7), 7.92 (td, 1H, 3JH-H = 3JH-F = 8.7 Hz, 4JH-H = 3.0 Hz, H-7). 13C NMR (126 MHz, CDCl3) δ 189.08(1C, CHO), 161.21 (d, 1C, 1JC-F = 250 Hz, C-6), 149.60 (d, 1C, 4JC-F = 3 Hz, C-8a), 146.82 (1C,C-2 or C-3), 139.65 (d, 1C, 4JC-F = 6Hz, C-4), 131.34 (d, 1C, 3JC-F = 9 Hz, C-8), 127.49 (d, 1C, 3JCF= 10 Hz, C-4a), 127.05 (1C, C-2 or C-3), 123.98 (d, 1C, 2JC-F = 26 Hz, C-7), 112.80 (d, 1C, 2JCF= 22 Hz, C-5). 19F NMR (470 MHz, CDCl3) δ-110.89. HRMS (ESI) m/z 210.0113 [M+H]+(calculated for [C11H6ClFNO]+ 210,0116), 242.0375 [M+32] (calculated for [C11H10ClFNO2]+242.0384, methyl hemiacetal form).
With trichlorophosphate 1.) 0 deg C, 0.5 h, 2.) 70 deg C, 16 h; Multistep reaction;
With trichlorophosphate
With trichlorophosphate Heating;
With trichlorophosphate at 0 - 82℃; for 24h; Inert atmosphere;
With trichlorophosphate at 75℃; for 8h; 4.2. General procedure for the synthesis of compounds 2a-2f General procedure: POCl3 (9.0 mL, 96 mmol) was added dropwise to DMF (2.8 mL,36 mmol) precooled at 0 C. Followed by adding acetanilide(10 mmol), the mixture was heated to 75 °C and stirred at thattemperature for 8 h. After been cooled to room temperature, themixture was poured to 100mL of ice-water. The precipitate wasobtained by suction filtration, washed with cold water and dried toafford the product.1H NMR and 13C NMR data of selected productsare shown as follows.
With trichlorophosphate for 24h; Heating;
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.25h; Stage #2: N1-(4-Fluorophenyl)acetamide at 80℃; for 8h;
With trichlorophosphate for 6h; Reflux;

Reference: [1]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]
[2]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]
[3]Fernández-Galleguillos, Carlos; Saavedra, Luis A.; Gutierrez, Margarita [Journal of the Brazilian Chemical Society, 2014, vol. 25, # 2, p. 365 - 371]
[4]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - US2019/308978, 2019, A1 Location in patent: Paragraph 0849; 0850
[5]Arnaud, Lucie; Chezal, Jean-Michel; Deuther-Conrad, Winnie; Dukic-Stefanovic, Sladjana; Kopka, Klaus; Lai, Thu-Hang; Maisonial-Besset, Aurélie; Miot-Noirault, Elisabeth; Roux, Valérie; Teodoro, Rodrigo; Weber, Valérie; Wenzel, Barbara [Molecules, 2022, vol. 27, # 12]
[6]Lavergne, Olivier; Lesueur-Ginot, Laurence; Rodas, Francesc Pla; Kasprzyk, Philip G.; Pommier, Jacques; Demarquay, Danièle; Prévost, Grégoire; Ulibarri, Gérard; Rolland, Alain; Schiano-Liberatore, Anne-Marie; Harnett, Jeremiah; Pons, Dominique; Camara, José; Bigg, Dennis C. H. [Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5410 - 5419]
[7]Khunt, Ranjan C.; Khedkar, Vijay M.; Coutinho, Evans C. [Chemical Biology and Drug Design, 2013, vol. 82, # 6, p. 669 - 684]
[8]Raghavan, Saiharish; Manogaran, Prasath; Gadepalli Narasimha, Krishna Kumari; Kalpattu Kuppusami, Balasubramanian; Mariyappan, Palanivelu; Gopalakrishnan, Anjana; Venkatraman, Ganesh [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3601 - 3605]
[9]Govender, Hogantharanni; Mocktar, Chunderika; Koorbanally, Neil A. [Journal of Heterocyclic Chemistry, 2018, vol. 55, # 4, p. 1002 - 1009]
[10]Zhao, Yan; Li, Min; Li, Bowen; Zhang, Shun; Su, Aoze; Xing, Yongning; Ge, Zemei; Li, Runtao; Yang, Baoxue [European Journal of Medicinal Chemistry, 2019, vol. 172, p. 131 - 142]
[11]Govender, Hogantharanni; Mocktar, Chunderika; Kumalo, Hezekiel M.; Koorbanally, Neil A. [Phosphorus, Sulfur and Silicon and the Related Elements, 2019, vol. 194, # 11, p. 1074 - 1081]
[12]Li, Jingyi; Ling, Fei; Lu, Yin-Jie; Shao, Bingxuan; Xiao, Xiao; Yang, Zehui; Zhong, Weihui [Chemical Communications, 2021, vol. 57, # 38, p. 4690 - 4693]
[13]Kumar, Vasantha; Rai, Vaishali M.; Udupi, Vishwanatha; Shivalingegowda, Naveen; Pai, Vinitha R.; Krishnappagowda, Lokanath Neratur; Poojary, Boja [Journal of the Iranian Chemical Society, 2022, vol. 19, # 3, p. 793 - 808]
  • 2
  • [ 326-65-8 ]
  • [ 33513-42-7 ]
  • [ 749920-54-5 ]
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  • [ 749920-54-5 ]
  • [ 4949-44-4 ]
  • diethyl 4-(6-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)-2,6-dimethyl-4H-pyran-3,5-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 7h; General experimental procedure for the synthesis of polysubstituted quinolone conjugated4H-pyrans 3a-l General procedure: To the stirred solution of 2-chloroquinoline-3-carbaldehydes 1a-f (1.0 mmol) in anhydrous DMF (4 mL)in a 10 mL round bottom flask; the β-keto ester 2a-d (2.0 mmol), Cs2CO3 (3.0 mmol) and Cu(OAc)2 (0.1mmol) were added at room temperature and the reaction mixture was heated at 100 °C for 7 h. Theprogress of the reaction was monitored through TLC (SiO2, hexane/EtOAc = 5:5). After completion ofreaction the reaction mixture poured in to 10 mL EtOAc and 5 mL H2O and extracted with EtOAc (3 × 15mL). The combined organic layer was dried over anhydrous Na2SO4. Solvent was removed under reducedpressure and the remaining residue was purified through silica gel (60-120 mesh) column chromatography(eluent; hexane/EtOAc = 70:30, v/v) to obtain the desired products 3a-l in high yields
  • 4
  • [ 703-80-0 ]
  • [ 749920-54-5 ]
  • C20H12ClFN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 3-acetylindole at 25℃; for 0.166667h; Stage #2: 2-chloro-6-fluoro-quinoline-3-carboxaldehyde With hydrogenchloride In water at 25℃; for 10h; Experimental procedure: General procedure: 1-(1H-Indole-3-yl) ethanone(1 mmol) was dissolved in PEG-400 as a reaction solvent (3mL). To this was added, bleaching earth clay (pH 12.5) (10mol%) and the mixture was stirred for 10 min at room temperature.Substituted chloroquinoline-3-carbaldehyde (1 mmol)was then added to the reaction mixture and stirred at 25 C for10 h and then poured onto crushed ice (25 g) and acidifiedwith 10% aqueous HCl. The organic mass was extracted withdichloromethane and washed with water. The extract was driedwith anhydrous Na2SO4 and concentrated to get the product(Scheme-I). The purification of compounds (3a-g) was carriedout using a silica gel (E. Merck 100-200 mesh column in CHCl3:CH3OH, 9:1).
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