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[ CAS No. 73568-35-1 ] {[proInfo.proName]}

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Product Details of [ 73568-35-1 ]

CAS No. :73568-35-1 MDL No. :MFCD08706312
Formula : C10H5BrClNO Boiling Point : -
Linear Structure Formula :- InChI Key :DCZCMZVZWKXJAF-UHFFFAOYSA-N
M.W : 270.51 Pubchem ID :11437167
Synonyms :

Safety of [ 73568-35-1 ]

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 [ 73568-35-1 ]

* 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.

  • Downstream synthetic route of [ 73568-35-1 ]

[ 73568-35-1 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 103-88-8 ]
  • [ 33513-42-7 ]
  • [ 73568-35-1 ]
YieldReaction ConditionsOperation in experiment
90% With cetyltrimethylammonim bromide; trichlorophosphate In acetonitrile for 1.41667h; Heating;
85% With trichlorophosphate at 0 - 90℃;
75% 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.
74% With trichlorophosphate at 80 - 90℃; for 12h; General procedure for synthesis of 2-chloroquinoline-3-carbaldehydes 3 To stirred DMF (3.6 mL, 46 mmol), 12.5 mL POCl3 (134 mmol) were added dropwise at 0-5 °C. The mixture was allowed to stir for 30 min. Acetanilide 2 (18.5 mmol) was then added and the resulting solution heated for 12 h at 80-90 °C. The mixture was poured into ice-cold water and stirred for 10 min, which resulted in yellow precipitation of the desired 2-chloroquinoline-3-carbaldehydes 3. The precipitate was filtered and washed with water and then dried. The compounds were purified by recrystallization from ethyl acetate.
68% With trichlorophosphate In 1,2-dichloro-ethane at 40℃; for 1h; ultrasound irradiation;
60% Stage #1: 4-bromoacetanilide; N,N-dimethyl-formamide With trichlorophosphate at 75℃; for 48h; Inert atmosphere; Stage #2: With water
45% With trichlorophosphate at 85℃; for 24h;
35% With trichlorophosphate at 80 - 90℃; for 16h;
35% With trichlorophosphate at 0 - 80℃; for 16h;
28% Stage #1: N,N-dimethyl-formamide With phosphorus pentachloride at 0℃; for 0.25h; Stage #2: 4-bromoacetanilide for 4h; Reflux; Synthesis of 2-chloroquinoline-3-carbaldehydes 5a-i General procedure: Dimethylformamide (12 mmol, 3 equiv.) was cooled at 0°C in a round flask equipped with a drying tube and phosphorus pentachloride (18 mmol, 4.5 equiv.) was added slowly and the mixture was stirred for 15 minutes keeping the temperature below 0°C. To this solution was added in a portion the corresponding acetanilide (4 mmol, 1 equiv.) and the reaction mixture was heated under reflux and stirring for the appropiate time depending of the acetanilide. The resulted mixture was cooled to 0°C and the solution was poured slowly into ice-water and stirring for ten minutes, obtaining a yellow solid which was filtered, washed several time with cold water and dried under vacuum. The 2-chloroquinoline-3-carbaldehydes were recrystallized according to the literature.
27% Stage #1: N,N-dimethyl-formamide With trichlorophosphate at -5℃; Inert atmosphere; Stage #2: 4-bromoacetanilide at 80℃; Inert atmosphere; 5.2.1. 2-chloroquinoline-3-carbaldehyde (2a) General procedure: Phosphorus oxychloride (19 ml, 207.16 mmol) was added drop wise at -5°C to DMF (7 ml, 88 mmol) under N2, then the acetanilide 1a(4.000 g, 29.59 mmol) was added at room temperature. The mixture was stirred overnight at 80 °C, then slowly poured on ice, filtered and dried to obtain compound 2a as light yellow solid; yield (5.100 g, 90%)Rf (15% EtOAc/Hexane)- 0.56.
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; Stage #2: 4-bromoacetanilide for 16h; Heating;
With trichlorophosphate at 75℃; for 48.5h; Inert atmosphere; Sealed tube; Cooling with ice; II.1 Step 1; DMF (54 ml, 701 mmol, 2.5 eq.) was added dropwise (via a syringe pump) to phosphoryl trichloride (179 ml, 1962 mmol, 7.0 eq.) in a 350 mL sealed tube in an ice bath under nitrogen. After the addition, the water bath was removed and N-(4-bromophenyl) acetamide (60 g, 280 mmol) was added in one portion and the resulting mixture was stirred until a homogenous solution was observed (approx. 30 min.). The reaction vessel was sealed and heated at 75 °C for 48 h. The reaction was allowed to cool and slowly poured onto ice (final volume of 2 L) and stirred for 25 min. The solid was filtered and washed with water until the filtrate was no longer acidic (~3 L) and the product was dried in an oven vacuum overnight at 50 °C to afford a light tan/gold colored solid, 6-bromo-2- chloroquinoline-3 -carbaldehyde.
Stage #1: N,N-dimethyl-formamide With trichlorophosphate Cooling with ice; Sealed tube; Inert atmosphere; Stage #2: 4-bromoacetanilide at 75℃; for 48.5h; Stage #3: With water Cooling with ice; 7.3 Step 3: MN-dimethylformamide (54 ml, 0.70 mol) was added dropwise (via a syringe pump) to phosphoryl trichloride (179 ml, 1.96 mol) in a 350 mL sealed tube in an ice bath under nitrogen. After the addition, the water bath was removed and N-(4- bromophenyl)acetamide (60 g, 0.28 mol) was added in one portion and stirred until a homogenous solution was observed (approx. 30 min.). The reaction vessel was sealed and heated at 75 °C for 48 h. The reaction was allowed to cool and slowly poured onto ice (final volume of 2 L) and stirred for 25 min. The solid was filtered and washed with water until the filtrate was no longer acidic (~3 L) and the product was dried in an oven vacuum overnight at 50 °C to afford 6-bromo-2-chloroquinoline-3-carbaldehyde as a light tan colored solid.
With trichlorophosphate
With trichlorophosphate at 0℃; Reflux; General procedure for the synthesis of 6-substituted-2-chloroquinoline-3-carbaldehydes 2a-d (Meth-Cohnet al., 1981) General procedure: Dimethylformamide 9.6 mL (0.125 mol)was cooled to 0 C, and phosphoryl chloride 32.2 mL(0.35 mol) was added drop-wise with stirring. To thissolution was added substituted acetanilide 1a-d (0.05 mol)and the reaction mixture was refluxed for 16-17 h. Reactioncompletion was monitored by TLC. The reactionmixture was poured into ice water (300 mL) and stirred for30 min at 0-10 °C. The resulting suspension was filteredand washed with water to give the intermediates 2a-d.
With trichlorophosphate
With trichlorophosphate for 24h; Heating;
With trichlorophosphate at 70 - 80℃; for 16h; Preparation of 2-chloroquinolin-3-carbaldehyde (6c-i) General procedure: Vilsmeir-Haack adduct was prepared by adding phosphorous oxychloride (0.35 mol) drop wise to the cold solution of DMF (0.125 mol) with constant stirring. To this adduct, substituted acetanilide (0.05 mol) was added slowly and stirred well for 15-20 min. The mixture was then refluxed for 16 h at 70-80°C. After completion of the reaction, the contents were poured into ice water and stirred for 30 min. The 2-chloroquinoline-3-carbaldehyde 6c-i precipitated out was filtered and washed well with water. Dried and recrystallized from ethyl acetate.
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.25h; Stage #2: 4-bromoacetanilide at 80℃; for 8h;
With trichlorophosphate for 6h; Reflux;
With trichlorophosphate at 80 - 90℃;

Reference: [1]Ali; Tasneem; Rajanna; Sai Prakash [Synlett, 2001, # 2, p. 251 - 253]
[2]Location in patent: experimental part Parab; Dixit; Desai [Asian Journal of Chemistry, 2011, vol. 23, # 6, p. 2725 - 2728]
[3]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]
[4]Mirjafary, Zohreh; Saidian, Hamid; Sahandi, Morteza; Shojaei, Leila [Journal of the Brazilian Chemical Society, 2014, vol. 25, # 7, p. 1253 - 1260]
[5]Moazzam Ali, Mir; Sana, Sariah; Tasneem; Rajanna; Saiprakash [Synthetic Communications, 2002, vol. 32, # 9, p. 1351 - 1356]
[6]Location in patent: experimental part Cheng, Yuan; Judd, Ted C.; Bartberger, Michael D.; Brown, James; Chen, Kui; Fremeau Jr., Robert T.; Hickman, Dean; Hitchcock, Stephen A.; Jordan, Brad; Li, Vivian; Lopez, Patricia; Louie, Steven W.; Luo, Yi; Michelsen, Klaus; Nixey, Thomas; Powers, Timothy S.; Rattan, Claire; Sickmier, E. Allen; St. Jean Jr., David J.; Wahl, Robert C.; Wen, Paul H.; Wood, Stephen [Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5836 - 5857]
[7]Fernández-Galleguillos, Carlos; Saavedra, Luis A.; Gutierrez, Margarita [Journal of the Brazilian Chemical Society, 2014, vol. 25, # 2, p. 365 - 371]
[8]Srivastava, Ambika; Singh [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875]
[9]Şişman, İlkay; Arkan, Burcu; Arslan, Barış Seçkin; Avcı, Davut; Derin, Yavuz; Gezgin, Merve; Nebioğlu, Mehmet; Tutar, Ahmet [Journal of Photochemistry and Photobiology A: Chemistry, 2021, vol. 404]
[10]Romero, Angel H. [Synthetic Communications, 2016, vol. 46, # 3, p. 287 - 291]
[11]Karkara, Bidhu Bhusan; Mishra, Shashank Shekhar; Panda, Gautam; Singh, Bhupendra N. [Bioorganic Chemistry, 2020, vol. 99]
[12]Location in patent: experimental part Mathada, Basavarajaiah Suliphal Devara; Mathada, Mruthyunjayaswamy Bennikallu Hire [Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 6, p. 557 - 560]
[13]Current Patent Assignee: AMGEN INC - WO2011/63233, 2011, A1 Location in patent: Page/Page column 35
[14]Current Patent Assignee: AMGEN INC - WO2011/63272, 2011, A1 Location in patent: Page/Page column 46-47
[15]Joshi; Hallikeri; More, Uttam A.; Basavaraj; Kulkarni [Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 1, p. 69 - 72] Khunt, Ranjan C.; Khedkar, Vijay M.; Coutinho, Evans C. [Chemical Biology and Drug Design, 2013, vol. 82, # 6, p. 669 - 684]
[16]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]
[17]Insuasty, Daniel; Robledo, Sara M.; Vélez, Iván D.; Cuervo, Paola; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo; Abonia, Rodrigo [European Journal of Medicinal Chemistry, 2017, vol. 141, p. 567 - 583]
[18]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]
[19]Nesaragi, Aravind R.; Kamble, Ravindra R.; Bayannavar, Praveen K.; Shaikh, Saba Kauser J.; Hoolageri, Swati R.; Kodasi, Barnabas; Joshi, Shrinivas D.; Kumbar, Vijay M. [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]
[20]Li, Jingyi; Ling, Fei; Lu, Yin-Jie; Shao, Bingxuan; Xiao, Xiao; Yang, Zehui; Zhong, Weihui [Chemical Communications, 2021, vol. 57, # 38, p. 4690 - 4693]
[21]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]
[22]Insuasty, Daniel; García, Stephanie; Abonia, Rodrigo; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo; Borosky, Gabriela L.; Laali, Kenneth K. [Archiv der Pharmazie, 2021, vol. 354, # 9]
  • 2
  • [ 73568-35-1 ]
  • [ 395057-56-4 ]
  • <i>N</i>-(6-bromo-2-chloro-quinolin-3-ylmethylene)-<i>N</i>'-[3-(4-methoxy-phenyl)-[1,8]naphthyridin-2-yl]-hydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With acetic acid In methanol for 0.05h; microwave irradiation;
  • 3
  • [ 73568-35-1 ]
  • [ 887922-71-6 ]
YieldReaction ConditionsOperation in experiment
83% With hydrogenchloride; sodium sulfide In ethanol Heating;
  • 4
  • [ 867-13-0 ]
  • [ 73568-35-1 ]
  • [ 1298044-13-9 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: 6-bromo-2-chloro-3-formylquinoline In tetrahydrofuran for 2h; stereoselective reaction;
  • 5
  • [ 73568-35-1 ]
  • [ 843663-66-1 ]
  • [ 857086-94-3 ]
  • 6
  • [ 73568-35-1 ]
  • [ 75-64-9 ]
  • [ 1308870-06-5 ]
YieldReaction ConditionsOperation in experiment
92% In 1-methyl-pyrrolidin-2-one at 130℃; for 24h; Inert atmosphere;
In 1-methyl-pyrrolidin-2-one at 130℃; for 24h; Sealed tube; 8.3 Step 3:; 6-Bomo-2-chloroquinoline-3-carbaldehyde (10 g, 37.0 mmol) was dissolved in NMP 200 mL in a 350 mL sealable flask. 2-Methylpropan-2-amine (23 mL, 217 mmol) was added and the reaction mixture was sealed to heated at 130 °C for 24 h. After cooling, the mixture was poured into IN HC1 200 mL and stirred for 1.5 h. The reaction was completed. The precipitates was isolated by filtration and washed with water. The solid was collected and dried on vacuum pump overnight to give 6-bromo-2-(teri- butylamino)quinoline-3-carbaldehyde as a yellow solid.
In 1-methyl-pyrrolidin-2-one at 130℃; for 16h; Sealed tube; 7.4 Step 4: 6-Bromo-2-chloroquinoline-3-carbaldehvde (10 g, 37 mmol) and 2-methylpropan- 2-amine (23 ml, 222 mmol) in W-Methyl-2-pyrrolidone (200 mL) was heated at 130 °C in a sealed tube for 16 h. The mixture was poured into water and the product precipitated. The solid was isolated by filtration and washed with water and dried on vacuum pump overnight to afford 2-(4-methoxybenzylamino)-6-bromoquinoline-3-carbaldehyde
In 1-methyl-pyrrolidin-2-one at 130℃; for 24h; sealed flask; 29.1 6-Bomo-2-chloroquinoline-3-carbaldehyde (10 g, 37.0 mmol) was dissolved in NMP 200 mL in a 350 mL sealable flask. 2-Methylpropan-2-amine (23 mL, 217 mmol) was added and the reaction mixture was sealed to heated at 130 °C for 24 h. After cooling, the mixture was poured into IN HC1 200 mL and stirred for 1.5 h. The reaction was completed. The precipitate was isolated by filtration and washed with water. The solid was collected and dried on vacuum pump overnight to give 6-bromo-2-(teri- butylamino)quinoline-3-carbaldehyde as a yellow solid.

  • 7
  • [ 1308870-29-2 ]
  • [ 73568-35-1 ]
  • [ 1308870-31-6 ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.5h; 10.3 Step 3: Triethyl phosphite (3.0 mL, 17.2 mmol) and 4-(l-bromoethyl)-6-ethylpyrimidine (0.66 g, 3.1 mmol) were combined in a reaction flask. Sodium iodide (0.15 g, 1.0 mmol) was added and the mixture heated to 150 °C. After 30 min the mixture was cooled.Purification using low pressure silica chromatography (0-10% MeOH in DCM gradient) gave a diethyl l-(6-ethylpyrimidin-4-yl)ethylphosphonate. The material was dried under high vac at 100 °C for 45 min to remove trace phosphite. 6-Bromo-2-chloroquinoline-3- carbaldehyde (0.51 g, 1.9 mmol) was dissolved in dry THF (40 mL) and added to the phosphonate. Potassium tert-butoxide (0.25 g, 2.3 mmol) was added and the reaction was stirred for 30 min. Saturated ammonium chloride (20 mL) and EtAOc (100 mL) were added and the mixture stirred. Water (100 mL) was added and the phases mixed and separated. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using low pressure silica chromatography (hexane to EtOAc gradient) gave 6-bromo-2-chloro-3-(2-(6-ethylpyrimidin-4-yl)prop-l- enyI)quino.ine.
  • 8
  • [ 73568-35-1 ]
  • [ 1017464-16-2 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; ethanol at 0 - 20℃; for 0.666667h; 2.2 Step 2: 6-Bromo-2-chloroquinoline-3-carbaldehvde (6.0 g, 22.2 mmol) was suspended in EtOH (65 mL). The solution was cooled to 0 °C and treated with sodium borohydride (1.26 g, 33.3 mmol). The reaction was warmed to RT and stirred for 40 min. The mixture was quenched with 30 mL saturated NaHC03 solution and followed by 100 mL H20. After gas evolution ceased, diluted with 250 mL EtOAc and washed with 2x water, 2x saturated NaHC03 solution, and 2x brine. The organics were then dried over Na2S04 and concentrated to afford (6-bromo-2-chloroquinolin-3-yl) methanol as a yellow solid.
With sodium tetrahydroborate In methanol at 20℃; 4.2.3 General procedure for the synthesis of (2-chloroquinolin-3-yl) methanol (4c-g) General procedure: To the well stirred mixture of 2-chloroquinoline-3-carbaldehyde 3c-g (0.01mol) in methanol (10ml), NaBH4 (0.01mol) was added in small portions, and the mixture was stirred at room temperature for 15-20min. The completion of the reaction was monitored by TLC and the reaction mixture was concentrated under vacuum. The mixture was poured into ice cold water and the (2-chloroquinolin-3-yl) methanol 4c-g separated as solid was filtered off and recrystallised from ethyl acetate.
With sodium tetrahydroborate In methanol at 20℃;
With sodium tetrahydroborate In methanol at 20℃; Preparation of 3-azidomethyl-2-chloro-6/7/8-substituted quinoline (7c-i) General procedure: To a well stirred mixture of 2-chloroquinoline-3-carbaldehyde (2c-i) (0.01 mol) in methanol (10 ml), NaBH4 (0.01 mol) was added in small portions and the mixture was stirred at room temperature for 15-20 min. The completion of the reaction was monitored by TLC and the reaction mixture was concentrated under vacuum. The mixture was poured into ice cold water and the (2-chloroquinolin-3-yl) methanol separated as solid was filtered off and recrystallised from ethyl acetate. (2-Chloroquinolin-3-yl) methanol (0.01 mol) was further dissolved in DCM (10-15 ml) at 5°C and stirred well. After 10-15 min, PBr3 (0.06 mol) was added drop wise and stirred at room temperature for 1 h. After completion of the reaction, DCM was removed under vacuum and the mixture was poured into ice and neutralized by adding a saturated solution of NaHCO3. The precipitate of 3-(bromomethyl)-2-chloroquinoline was filtered and dried. The so formed 3-(bromomethyl)-2-chloro quinoline (0.010 mole) was taken in acetone (20 ml) in a round-bottom flaskamnd to this sodium azide (0.012 mole) in water (3.00 ml) was added drop wise with stirring, which was continued for 10 hr. The reaction mixture was then poured into ice-cold water. 3-Azidomethyl-2-chloro-6/7/8-substituted-quinoline 7c-i separated as solid was filtered and recrystallized using ethanol.
With sodium tetrahydroborate In methanol at 20℃;

  • 9
  • [ 73568-35-1 ]
  • [ 2393-23-9 ]
  • [ 1309365-83-0 ]
YieldReaction ConditionsOperation in experiment
91% In ethanol at 125℃; for 2.5h; Inert atmosphere;
72.9% Stage #1: 6-bromo-2-chloro-3-formylquinoline; 4-methoxy-benzylamine In ethanol at 90 - 95℃; for 48h; Sealed tube; Stage #2: With hydrogenchloride In ethanol; water at 90℃;
In ethanol at 125℃; for 2.5h; Sealed tube; II.2 Step 2; 6-Bromo-2-chloroquinoline-3-carbaldehyde (10.0 g, 37.0 mmol) and 4- methoxybenzylamine (14.4 ml, 1 10.9 mmol) in EtOH (200 mL) was heated at 125 °C in a sealed tube for 2.5 hours. The reaction mixture was cooled and poured into IN HCl (200 mL) and stirred 2 h. The mixture was extracted with chloroform and the combined organic layers was washed with IN HCl and brine, dried over sodium sulfate, filtered and concentrated to afford 2-(4-methoxybenzylamino)-6-bromoquinoline-3-carbaldehyde 7.
  • 10
  • [ 73568-35-1 ]
  • [ 1309366-04-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1-methyl-pyrrolidin-2-one / 24 h / 130 °C / Sealed tube 2: lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 10 h / 20 °C 3: potassium acetate / bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) / ethanol; water / 2 h / 80 °C 4: hydrogen / palladium on carbon / methanol
Multi-step reaction with 4 steps 1: 1-methyl-pyrrolidin-2-one / 24 h / 130 °C / Sealed tube 2: potassium carbonate / ethanol / 1 h / 80 °C 3: potassium acetate / bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) / ethanol; water / 2 h / 80 °C 4: hydrogen / palladium on carbon / methanol
Multi-step reaction with 4 steps 1: 1-methyl-pyrrolidin-2-one / 24 h / 130 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 10 h / 20 °C / Inert atmosphere 3: bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II); water; potassium acetate / ethanol / 2 h / 80 °C / Inert atmosphere 4: palladium on activated charcoal; hydrogen / methanol / Inert atmosphere
  • 11
  • [ 73568-35-1 ]
  • [ 1309366-05-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 1-methyl-pyrrolidin-2-one / 24 h / 130 °C / Sealed tube 2.1: lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 10 h / 20 °C 3.1: potassium acetate / bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) / ethanol; water / 2 h / 80 °C 4.1: hydrogen / palladium on carbon / methanol 5.1: sodium hydroxide; water / methanol / 3 h / Reflux 5.2: 20 °C / pH 2 - 3
Multi-step reaction with 5 steps 1.1: 1-methyl-pyrrolidin-2-one / 24 h / 130 °C / Sealed tube 2.1: potassium carbonate / ethanol / 1 h / 80 °C 3.1: potassium acetate / bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II) / ethanol; water / 2 h / 80 °C 4.1: hydrogen / palladium on carbon / methanol 5.1: sodium hydroxide; water / methanol / 3 h / Reflux 5.2: 20 °C / pH 2 - 3
Multi-step reaction with 5 steps 1: 1-methyl-pyrrolidin-2-one / 24 h / 130 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 10 h / 20 °C / Inert atmosphere 3: bis(di-tert-​butyl(4-​dimethylaminophenyl)​phosphine)​dichloropalladium(II); water; potassium acetate / ethanol / 2 h / 80 °C / Inert atmosphere 4: palladium on activated charcoal; hydrogen / methanol / Inert atmosphere 5: methanol; sodium hydroxide / 2 h / Reflux; Inert atmosphere
  • 12
  • [ 73568-35-1 ]
  • [ 99465-04-0 ]
YieldReaction ConditionsOperation in experiment
With ammonia; iodine In tetrahydrofuran; water
Stage #1: 6-bromo-2-chloro-3-formylquinoline With hydroxylamine hydrochloride In tetrahydrofuran; water at 20℃; for 1h; Stage #2: With thionyl chloride In chloroform for 1h; Reflux; 4.3. General procedure for the synthesis of compounds 3a-3f General procedure: To a solution of hydroxylamine hydrochloride (520 mg,7.5 mmol) in 1mL water, compound 2a-2f (1.65 g, 7.5 mmol) in15 mL THF was added. The reaction mixture was stirred at roomtemperature for 1 h. THF was removed under vacuum. The residuewas stirred in 10 mL water for 10 min. Solid precipitated wasfiltered and dried. The dried solid was dissolved in 15 mL of chloroformand SOCl2 (1.4 mL, 15 mmol) was add slowly to the solution.After refluxing for 1 h, the mixture was concentrated and the residuewas recrystallized with ethanol to give pure product. 1H NMRand 13C NMR data of selected products are shown as follows.
  • 13
  • [ 73568-35-1 ]
  • [ 112575-84-5 ]
  • [ 1228269-06-4 ]
YieldReaction ConditionsOperation in experiment
75% With acetic acid In methanol for 0.025h; Microwave irradiation; Capped flask;
  • 14
  • [ 73568-35-1 ]
  • [ 2365-48-2 ]
  • [ 918145-24-1 ]
YieldReaction ConditionsOperation in experiment
71% With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 1h;
  • 15
  • [ 53524-88-2 ]
  • [ 73568-35-1 ]
  • [ 941670-19-5 ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Reflux; General procedure: Naphtho[2,1-b]furan-2-carbohydrazide (0.01 mol) 3, 2-chloro-3-formylquinoline 4a (0.01 mol) weretaken in ethanol with catalytic amount of acetic acid (20 ml) and heated to refluxed for 3-4 hrs.After conclusion of the reaction (TLC), the reaction mixture was poured onto crushed ice; thesolid mass thus separated out was filtered, washed with water and dried to give the desiredcompounds 5a in 70-75% yields.
  • 16
  • [ 73568-35-1 ]
  • [ 17823-27-7 ]
  • [ 1446868-09-2 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate In ethanol Reflux; General Procedure for the Synthesis of Compounds (3a-k) General procedure: A mixture of the 2-(phenylimino)thiazolidin-4-one (1) (0.01 mol), substituted quinoline (2a-k) (0.01 mol) and fused sodium acetate (0.02 mol) was taken in 25 mL of absolute ethanol and refluxed for 6-10 hours. The mixture was then poured into 100 mL water and kept overnight. The precipitate obtained was filtered, washed with water and crystallized from chloroform to give compound (3a-k). Yield of the products varied between 57 and 70 %.
  • 17
  • [ 73568-35-1 ]
  • C10H6BrClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 20℃; for 0.75h; General procedure for the synthesis of 3-(2-chloroquinolin-3-yl)-5-phenylisoxazol (3a-j) General procedure: The corresponding precursor, 2-chloroquinolin-3-carbaldehyde (2a-j) (1.0 equiv.) was added to a hydroxylamine solution (1.1 equiv.) in ethanol. Then NaOH was added (1.1 equiv.) to the reaction mixture, which was then stirred at room temperature for 45 minutes. The oxyme formation was corroborated by thin-layer chromatographic (TLC) analysis. Chloramine-T trihydrate (1.1 equiv.) was added, followed by CuSO4∘5H2O (0.03 equiv.) and Cu (0.01 equiv.). When a change of color was observed, 10 mL of THF followed by phenylacetylene (1.1 equiv.) were added to the solution and stirred for 8 hours. Once finished, the reaction was filtered to remove copper salts, washed with water, dried with anhydrous Na2SO4 and recrystallized from ethanol. The derivatives which could not be purified using recrystallization techniques were purified using column chromatography in silica gel, using an 8:2 Hexane/EtOAc mixture as the mobile phase, except the derivative 2d, which was purified using only dichloromethane as the mobile phase.
  • 18
  • [ 106-40-1 ]
  • [ 73568-35-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / Reflux 2: trichlorophosphate / 24 h / 85 °C
Multi-step reaction with 2 steps 1: 0.5 h / 40 - 50 °C 2: trichlorophosphate / 12 h / 80 - 90 °C
Multi-step reaction with 2 steps 1: acetic acid / 1 h / Reflux 2: trichlorophosphate / 24 h / Heating
Multi-step reaction with 2 steps 1: sodium carbonate / dichloromethane / 3 h / 0 - 20 °C 2: trichlorophosphate / 16 h / 0 - 80 °C
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 °C 2: trichlorophosphate / 6 h / Reflux

  • 19
  • [ 73568-35-1 ]
  • [ 126-81-8 ]
  • C18H14BrNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With potassium fluoride on basic alumina In acetonitrile at 80 - 90℃; for 10h; General procedure for synthesis of pyranoquinolines 5 To a stirred suspension of 100 mg KF-Al2O3 in acetonitrile (5 mL) were added 2-chloroquinoline-3-carbaldehyde 3 (1 mmol) and dimedone (140 mg, 1 mmol). The reaction mixture was stirred at 80-90 °C for 10 h. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the solvent was removed under reduced pressure, and the residue was separated by preparative TLC (eluent:petroleum ether/ethyl acetate 5:1) to afford the desired compound 5.
  • 20
  • [ 73568-35-1 ]
  • [ 106-95-6 ]
  • [ 1404111-11-0 ]
YieldReaction ConditionsOperation in experiment
With indium In water; N,N-dimethyl-formamide at 20℃; General procedure: Indium metal (2.5 mmol) and allyl bromide (3 mmol) were added to a solution of aldehydes 1 (1 mmol) in DMF (8 ml)and stirred for 8-12 hrs. After completion of the reaction, the reaction mixture was quenched with a few drops of 2N HCl, diluted with water and extracted with ethyl acetate. The organic layer was dries from sodium sulphate, filtered and concentrated in vacuum. The products 2-chloro-3-homoallylquinolines 2 were recrystallized from ethyl acetate-hexane. The 2-chloro-3-homoallylquinolines 2 were dissolved in DMF and Na2S(1.5 equiv) was added in it. After completion of the reaction, acetic acid was added into the reaction mixture and the corresponding 2-thiones 3 precipitated out which was filtered out. The solid products were pure enough for further use.
  • 21
  • [ 558-13-4 ]
  • [ 73568-35-1 ]
  • 6-bromo-2-chloro-3-(2,2-dibromovinyl)-quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With triphenylphosphine In dichloromethane at 0℃; General procedure for the synthesis of 2-choro-3-(2,2-dibromo-vinyl)quinolines (2a-j) General procedure: Carbontetrabromide (2 equiv) and triphenylphosphine (2 equiv) were added to a solution of 2-chloroquinoline-3-carboxaldehydes 1 (1 mmol) in DCM (4 ml) at 0 oCand stirred for 20-40 min until total disappearance of the starting material as monitored by TLC. After completion of the reaction, DCM was evaporated and slurry was prepared. The pure product was obtained by column chromatography on silica gel using ethylacetate and hexane (1%) as eluents.
89% With triphenylphosphine In dichloromethane at 0℃; for 1h;
  • 22
  • [ 7188-38-7 ]
  • [ 73568-35-1 ]
  • [ 64-19-7 ]
  • [ 107-11-9 ]
  • C20H23BrClN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol at 20℃; General procedure for one-pot synthesis of 1H-pyrrolo[2,3-b]quinolines (6) General procedure: To a solution of substituted 2-chloroquinolin-3-carboxaldehydes 1 (1 mmol) in 5 mL methanol was added allyl amine (1.2 mmol), isocyanides (1 mmol), acetic acid (1.2 mmol) and the reaction mixture was stirred at room temperature for 12 h. The solution was concentrated under vacuum and the residue was redissolved under inert atmosphere in 5 mL of DMF. To the solution were added CuI (5 mol %), 1,10-phenanthroline (10 mol %) and K2CO3 (2 equiv) and the mixture was heated at 120 °C. After completion of the reaction, monitored by TLC, chilled water was poured in reaction mixture and extracted with ethyl acetate, dried over anhydrous sodium sulphate (Na2SO4) and concentrated under vacuum. The pure products 6a-l were obtained by column chromatography purification on silica gel(using varying ratios of EtOAc: hexane as eluent). Similar procedure was followed for synthesis of products 8a-c and 10a-b, using pyridine-3-carboxaldehyde 7 and naphthalene-2-carboxaldehyde 9 respectively.
  • 23
  • [ 103-88-8 ]
  • (4,6-dichloro-[1,3,5]triazin-2-yloxymethylene)-dimethyl-ammonium; chloride [ No CAS ]
  • [ 73568-35-1 ]
YieldReaction ConditionsOperation in experiment
86% In dichloromethane for 9h; Reflux; Cyclization reaction using TCTA-DMF reagent; General procedure: To the prepared TCTA-DMFreagent, 9.8 mmol of the Acetanilide was added and stirred under refluxconditions. Progress of the reaction was checked by TLC till the completion ofthe reaction. Analytical TLC was carried out using Merck aluminum-backed0.2 mm silica gel 60 F-254 plates. Column chromatography was conductedusing Merck silica gel 60 (230-400 mesh). After completion of the reaction,water was added to the reaction mixture and stirred for a few more minutes toextract inorganic components into water. The organic layer was separated andthe crude product thus obtained was further purified with columnchromatography (silica gel, ethyl acetate/n-hexane)
  • 24
  • [ 54-85-3 ]
  • [ 73568-35-1 ]
  • N'-[(6-bromo-2-chloroquinolin-3-yl)methylene]isonicotinohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With acetic acid In ethanol Reflux; General procedure for synthesis of N'-[(6-substituted-2-chloroquinolin-3-yl) methylene]isonicotinohydrazides 6a-d (Khalil et al., 1993) General procedure: A mixture of 2a-d (0.005 mol)and isoniazid (0.005 mol) in ethanol (20 mL) was refluxedfor 4-6 h in the presence of few drops of glacial aceticacid. The completion of reaction was detected by TLC.Solvent was evaporated under reduced pressure and pouredonto crushed ice, and the resultant solid was recrystallizedfrom ethanol and DMF mixture to give the products.
  • 25
  • [ 67-56-1 ]
  • [ 73568-35-1 ]
  • 6-bromo-2-methoxyquinoline-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With potassium hydroxide for 3h; Reflux;
76% 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).
  • 26
  • [ 6642-31-5 ]
  • [ 73568-35-1 ]
  • [ 126-81-8 ]
  • 6-amino-5-(9-bromo-3,3-dimethyl-1-oxo-2,3,4,12-tetrahydro-1H-chromeno[2,3-b]quinolin-12-yl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With <i>L</i>-proline In ethanol for 24h; Reflux; Typical Procedure for the preparation of compounds: General procedure: A dry 25 mL flask was charged with aldehyde (1.5 mmol), methylene active compound (1.5 mmol), 6-aminouracil (1 mmol), L-proline (0.1 mmol) and ethanol (5 mL). The mixturewas stirred at reux for 24 h. After reaction completion (TLC), the reactionmixture was cooled to room temperature. The mixture was ltered and theprecipitate washed with EtOH to afford the product. Physical data and spectraldata as well as copies of NMR for all compounds are provided in the ESI.
  • 27
  • [ 6642-31-5 ]
  • [ 73568-35-1 ]
  • [ 108-26-9 ]
  • wrong name: 6-amino-5-(7-bromo-3-methyl-1,4-dihydropyrazolo[4’,3’:5,6]quinolin-4-yl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With <i>L</i>-proline In ethanol for 24h; Reflux; Typical Procedure for the preparation of compounds: General procedure: A dry 25 mL flask was charged with aldehyde (1.5 mmol), methylene active compound (1.5 mmol), 6-aminouracil (1 mmol), L-proline (0.1 mmol) and ethanol (5 mL). The mixturewas stirred at reux for 24 h. After reaction completion (TLC), the reactionmixture was cooled to room temperature. The mixture was ltered and theprecipitate washed with EtOH to afford the product. Physical data and spectraldata as well as copies of NMR for all compounds are provided in the ESI.
  • 28
  • [ 24706-48-7 ]
  • [ 73568-35-1 ]
  • [ 108-26-9 ]
  • 9-bromo-5-(4-methoxyphenyl)-3,3-dimethyl-12-(5-methyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-3,4,5,12-tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With <i>L</i>-proline In ethanol Reflux; General procedure for the synthesis of compounds 7 General procedure: A dry 25 mL flask was charged with aldehyde (1.5 mmol), 3-methyl-1H-pyrazol-5(4H)-one (1 mmol), enaminone (1 mmol), L-proline(0.017 g, 0.15 mmol) and ethanol (5 mL). The mixture was stirred at reflux for the appropriate time. After reaction completion (TLC), the reaction mixture was cooled to room temperature. The mixture was filtered and the precipitate washed with EtOH to afford the product. Copies of NMR spectra for all compounds and HR mass spectra for some compounds are provided in the ESI.
  • 29
  • C11H8BrClN2O [ No CAS ]
  • [ 33513-42-7 ]
  • [ 73568-35-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N,N-dimethyl-formamide With trichlorophosphate Cooling; Stage #2: C11H8BrClN2O Reflux; 4.2.2 General procedure for the synthesis of 2-chloroquinolin-3-carbaldehyde (3c-g) General procedure: Vilsmeir-Haack adduct was prepared by adding phosphorous oxychloride (0.35mol) drop wise to the cold solution of DMF (0.125mol) with constant stirring. To this adduct, substituted acetanilide (0.05mol) was added slowly and stirred well for 15-20min. The mixture was then refluxed for 16hat 70-80°C. After completion of the reaction, the contents were then poured into ice water and stirred for 30min. The 2-chloroquinoline-3-carbaldehyde 3c-g was precipitated which was filtered and washed well with water. Dried and recrystallised from ethyl acetate.
  • 30
  • [ 73568-35-1 ]
  • [ 73568-45-3 ]
YieldReaction ConditionsOperation in experiment
With acetic acid Reflux;
With acetic acid In water Reflux; General procedure for the synthesis of N-methyl, N-phenyl and thiosemicarbazone derivatives (5a-o) General procedure: The substituted 2-chloroquinoline-3-carbaldehydes (3a-e)(1 mmol) was heated under reflux with 70% acetic acid (10 mL) for 4-6 h and upon cooling the product preciptated out of solution to form (4a-e). The thiosemicarbazone derivatives were then formed according to the method in Bisceglie et al.[31] Substituted thiosemicarbazides, 4-methylthiosemicarbazides or 4-phenylthiosemicarbazides(1.0 mmol) dissolved in methanol (80 mL) were added to an equivalent amount of 4a-e (200 mg; 1.0 mmol) and the solution stirred at room temperature for 24 h. Upon completion, the flask was placed in an ice bath, where a solid formed, which was filtered, washed with ethanol and dried.
  • 31
  • [ 73568-35-1 ]
  • [ 109-77-3 ]
  • [ 122-52-1 ]
  • C17H16BrClN3O3P [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine In ethanol at 80℃; for 10h; General procedure for the synthesis of β-phosphonomalonates General procedure: Triethylamine (2 mol%) was added to a mixture of substituted aldehydes 1 (1 mmol), malononitrile/ethyl cyanoacetate 2 (1 mmol), and phosphite ester 3 (1 mmol) in EtOH (4 mL). The contents of the reaction mixture were heated at 80 °C for an appropriate time (Table 2). After completion of the reaction as monitored by TLC, the crude product was isolated and purified by crystallization with ethanol. In some cases (Table 2, entries 7, 9, and 16) the crude product was purified by column chromatography using ethyl acetate and n-hexane (8:2 to 6:4).
  • 32
  • [ 931-53-3 ]
  • [ 73568-35-1 ]
  • 7-bromo-2-cyclohexyl-1-hydroxy-1H-pyrrolo[3,4-b]quinolin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With water; palladium diacetate; caesium carbonate In 1,4-dioxane at 50℃; for 4h;
  • 33
  • 1-(6-nitro-1H-benzimidazol-2-yl)ethanone [ No CAS ]
  • [ 73568-35-1 ]
  • C19H10BrClN4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In water at 20℃; for 0.5h; Synthesis of 3-(2-chloroquinolin-3-yl)-1-(6-nitro-1H-benzimidazol-2-yl)prop-2-en-1-one (IVa-k) General procedure: To a solution of compound III (10 mmol, 3.78 g) in 30 mL aqueous NaOH(10 %) was added to the respective 2-chloroquinoline-3-carbaldehyde (10 mmol, 1.91g) at room temperature. The reaction mixture was stirred for 0.5 h. At the end of this period, the separated solid was filtered, washed with distilled water and dried. The crude product thus obtained was recrystallized from suitable solvent [10-16].
  • 34
  • [ 41510-16-1 ]
  • [ 73568-35-1 ]
  • C19H10BrCl2N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In water at 20℃; for 0.5h; General procedure for the synthesis of chalcone derivative of 6-chlorobenzimidazoles (IVa) General procedure: To a reaction mixture of 6-chloro-2-acetylbenzimidazole (10 mmol, 1.94 g) in aqueous NaOH (10%, 30 ml), respective 2-chloroquinoline-3-carbaldehyde (10 mmol, 1.91 g) were added and agitated for 30 min. at an ambient temperature. After the conclusion of the reaction the solid product was filtered, washed and dried with water. Further, it was recrystallized from ethanol.
  • 35
  • 5-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl]-4-amino-4H-1,2,4-triazole-3-thiol [ No CAS ]
  • [ 73568-35-1 ]
  • 3-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl]-9-bromoquinolino[3,2-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate In N,N-dimethyl-formamide for 8h; Reflux; General procedure for the synthesis of 3-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl]-11-methylquinolino[3,2-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepines (7a): General procedure: 2-Chloro-8-methyl quinoline-3-carbaldehyde (2.05 g, 10 mmol) andpotassium carbonate (1.38 g, 10 mmol) were added in 5-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl]-4-amino-4H-1,2,4-triazole-3-thiol [34] (3.74 g, 10 mmol) in DMF (30 mL)as solvent and the reaction mixture was refluxed for 8 h. Itwas then concentrated and poured in icecold water and thesolid separated out was filtered and recrystallized from ethanol to get 7a as yellow amorphous solid (yield 82 %); m.p. 220 °C;m.f. C 30 H19N7OS. Correspondingly, other 3-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl]-substituted quinoline [3,2-f][1,2,4]-triazolo[3,4-b][1,3,4]thiadiazepines (7b-i) were synthesized from 4 and (6b-i) by similar procedure as followedfor 7a (Scheme-I).
  • 36
  • [ 1003-09-4 ]
  • [ 73568-35-1 ]
  • C14H9BrClNOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.3% Stage #1: 2-bromothiophene With iodine; magnesium In tetrahydrofuran at 20 - 40℃; for 0.666667h; Inert atmosphere; Stage #2: 6-bromo-2-chloro-3-formylquinoline In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; 2 Preparation of intermediate A2 In a 50 ml single-necked flask, magnesium dust (600 mg, 24.68 mmol) and a catalytic amount of iodine were added under a nitrogen atmosphere. 2-Bromothiophene (790 mg, 4.85 mmol) was dissolved in 10 ml of anhydrous THF and slowly added dropwise to a single-necked flask. The mixture was heated with a hair dryer under stirring to initiate a reaction. The internal temperature was controlled to not exceed 40 ° C, and the mixture was stirred at room temperature for 40 minutes. 2-Chloro-6-bromo - quinoline-3-carbaldehyde (870mg, 3.22mmol) was dissolved in 5ml of dry THF was added the reaction mixture stirred at room temperature 1h.The reaction was quenched by the addition of 5 ml of water and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (10 ml × 2). EtOAc (EtOAc m. Ethyl acetate/petroleum ether = 1/4) gave the A2 compound (750 mg, yield: 85.3%).
  • 37
  • [ 103-88-8 ]
  • [ 73568-35-1 ]
YieldReaction ConditionsOperation in experiment
90% With trichlorophosphate In N,N-dimethyl-formamide at 80℃; for 8h; Schlenk technique; Inert atmosphere;
  • 38
  • [ 4187-87-5 ]
  • [ 73568-35-1 ]
  • (Z)-7-bromo-2-(hydroxy(phenyl)methylene)-2,3-dihydro-1H-cyclopenta[b]quinolin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 9h; Schlenk technique; Inert atmosphere;
  • 39
  • [ 124-41-4 ]
  • [ 73568-35-1 ]
  • 6-bromo-2-methoxyquinoline-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In methanol for 3h; Reflux; Preparation of IV-1-1-1 Dissolve 6-bromo-2-chloroquinoline-3-carbaldehyde (5.0g, 18.52mmol) in MeOH (30ml),Add freshly prepared sodium methoxide methanol solution (93mmol) under ice bath,After the addition, the reaction was refluxed for 3h. TLC: petroleum ether: ethyl acetate = 10:1.After the reaction is completed, cool to room temperature, pour the reaction solution into ice water,The solids are separated out, filtered, and the filter cake is dried.Obtained pale yellow powdery solid: 4.0 g, yield: 80%.
37% In methanol at 70℃; 5.2.3. 2-methoxyquinoline-3-carbaldehyde (3a) General procedure: To a stirred solution of 2-chloroquinoline-3-carbaldehyde 2a (1.5gm, 7.82 mmole) in methanol, sodium methoxide (845 mg, 15.65mmole) was added slowly. Then reaction mixture was stirred at 70 °Cfor 1 hr. After completion of the reaction, methanol was evaporated.Then it was diluted with ethylacetate followed by water. The layers were seperated and the organic layer was dried over Na2SO4.
  • 40
  • [ 73568-35-1 ]
  • [ 95-84-1 ]
  • C17H12BrClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With acetic acid at 20℃; for 1h; Synthesis of (E)-2-((2-(6-bromo-2-chloroquinolin-3-yl) ethylidene) amino)-methylphenol, (3) A mixture of 6-bromo-2-chloroquinoline-3-carbaldehyde (5 g, 18.48 mmol) and 2-amino-p-cresol (2.27 g, 18.48 mmol) in acetic acid (50mL) was stirred at room temperature for 1 h. The progress of the reaction was monitored by thin layer chromatography (TLC) (hexane:ethyl acetate, 6:4). After completion of the reaction, acetic acid was removed under reduced pressure. The crude compound was washed with n-hexane and dried to provide the title compound 3 as yellow solid (7.0 g, 97%). Melting point: 204-206 °C; 1H NMR(400MHz, DMSO-d6): δ 9.38 (s, 1H, OH), 9.30 (s, 1H, H-C=N-, imine), 9.07 (s, 1H, quinoline-H), 8.46 (s, 1H, quinoline-H), 7.99 (dd, J=16.0 Hz, 2.4 Hz, 1H, quinoline-H), 7.95 (d, J=8.8 Hz, 1H, quinoline-H), 7.31 (dd, J=7.6 Hz, 1.60Hz, 1H, quinoline-H), 7.18-7.14 (m, 1H, phenol-H), 6.97 (d, 1H, J=8.0 Hz, phenol-H), 6.95-6.87 (m, 1H, phenol-H), 1.91 (s, 3H, methyl, CH3); 13C NMR (100MHz, DMSO-d6): δ 154.3 (CH, C15, imine), 151.9 (C, C2), 150.4 (C, C10), 146.6 (C, C12), 137.7 (C, C13), 135.5 (CH, C8), 131.5 (CH, C17), 130.3 (CH, C9), 129.0 (CH, C6), 128.9 (CH, C18), 128.6 (C, C10), 121.2 (C, C5), 120.8 (C-Br, C7), 120.1 (C, C3), 116.9 (CH, C19), 20.5 (methyl, CH3).
  • 41
  • [ 73568-35-1 ]
  • [ 95-55-6 ]
  • 2-bromobenzo[2,3][1,4]oxazepino[7,6-b]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h; N-(4-fluoro-2-methoxyphenyl)benzo[2,3][1,4]oxazepino[7,6-b]quinolin-2-amine, (6a) A mixture of 6-bromo-2-chloroquinoline-3-carbaldehyde (5 g, 18.48 mmol) and 2-amino phenol (2.02 g, 18.48 mmol) in dichloromethane (50 mL) was added DBU (5.62 g, 36.96 mmol) then stirred at room temperature for 2 h. The progress of the reaction was monitored by TLC (hexane:ethyl acetate, 1:1). After completion of the reaction, following the general procedure, a mixture of 6 (0.2 g, 0.615 mmol) in 1,4-dioxane (2 mL) was added 4-fluoro-2-methoxyaniline (95 mg, 0.676 mmol) and NaOtBu (88 mg, 0.922 mmol) followed by the addition of XPhosPdG2 Precatalyst (14.30 mg, 3 mol%) were heated at 90 °C in microwave irradiation for 45 min. The progress of the reaction was monitored by TLC (hexane:ethyl acetate, 6:4). The crude product was purified via the Biotage SP4 (silica packed 12 g snap cartridge column; 35% hexane/ethyl acetate as eluent) to provide the title compound (6a) as a Brown solid (98%). Melting point: 262.5-264.6 °C; 1HNMR (400 MHz, DMSO-d6): δ 8.62 (s, 1H, quinoline-H), 8.43 (s, 1H, H-C=N-, oxazepine), 7.94 (s, 1H, quinoline-H), 7.74 (d, 1H, J = 9.2 Hz, quinoline-H), 7.53 (d, 1H, J =8.8 Hz, 1-benzene-H), 7.39-7.31 (m, 5H, Ar-H), 7.12 (s,1H, quinoline-H), 7.03 (dd, 1H, J = 11.2 Hz, 2.8 Hz, quinoline-H), 6.80-6.75 (m, 1H, 1-benzene-H), 3.81 (s, 1H, -O-CH3, methoxy); 13C NMR (100 MHz, DMSO-d6): δ 160.5 (C, C2), 158.7 (CH, C15), 153.5 (C-F, C24), 149.8 (-C-OCH3, C26), 144.5 (C, C12), 141.8 (C, C13), 140.8 (2C, C7, and C10), 139.8 (C, C17), 129.4 (CH, C4), 128.7 (2CH, C18, and C28), 126.9 (CH, C22), 125.1 (CH, C18), 123.2 (2CH, C6, and C9), 122.5 (CH, C22), 121.4 (CH, C23), 107.1 (C, C3), 101.1 (CH, C25), 56.3 (-O-CH3, methoxy); 19F NMR (376.7 MHz, DMSO-d6): δ -116.84 (-C-F); LC-MS m/z calcd for C23H16FN3O2 is 385.39, found 386.0 [M + H].
  • 42
  • [ 73568-35-1 ]
  • [ 343338-28-3 ]
  • (S,E)-N-((6-bromo-2-chloroquinolin-3-yl)methylene)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.7% With copper(II) sulfate In 1,2-dichloro-ethane at 20 - 50℃; for 16h; 47.3 Step-3: Synthesis of (S,E)-N-((6-bromo-2-chloroquinolin-3-yl)methylene)-2-methylpropane-2-sulfinamide To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.0 g, 4.50 mmol, 1.0 eq.) and Copper (II) sulfate (1.43 g, 9.00 mmol, 2.0 eq.) in dichloroethane (20 mL) was added (S)-2-methylpropane-2-sulfinamide (2.18 g, 18.00 mmol, 4.0 eq.) at RT. The resulting mixture was heated at 50° C. for 16 h. Following this, reaction was allowed to cool to room temperature, filtered through celite pad, the celite pad washed with dichloromethane (30 mL). The combined filtrate dried over anhydrous Na2SO4 and concentrated under vacuum to get the solid residue which was purified by normal phase silica-gel column chromatography to get the title compound (1.25 g 85.7%). LCMS: 325.0 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 (s, 1H) 8.88 (s, 1H) 7.92 (d, J=9.21 Hz, 1H) 7.69 (d, J=2.63 Hz, 1H) 7.56 (dd, J=9.21, 3.07 Hz, 1H) 3.92 (s, 3H) 1.24-1.28 (m, 9H).
  • 43
  • [ 73568-35-1 ]
  • [ 623-51-8 ]
  • C14H10BrNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With triethylamine at 90℃; for 1h;
  • 44
  • [ 73568-35-1 ]
  • [ 63543-89-5 ]
  • 6‑bromo‑3‑(Z‑(Z‑4‑oxo‑2‑(phenylimino)‑3‑propylthiazolidin‑5‑ylidene)methyl)quinolin‑2(1H)‑one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With sodium acetate; acetic acid for 10h; Reflux; General procedure for the synthesis of (8a-o) General procedure: To a solution of 7a-c (0.01 moles), substituted 2-chloroquinoline-3-carboxaldehyde 3a-e (0.01 moles) and anhydroussodium acetate (0.025 moles) in glacial acetic acid(20 ml) was refluxed for 10 h. After completion of thereaction, it was cooled to room temperature. Resulting solid was filtered off, washed with water, dried and recrystallizedfrom N, N-dimethyl formamide.
  • 45
  • [ 73568-35-1 ]
  • [ 51347-26-3 ]
  • 3‑(Z‑(Z‑3‑benzyl‑4‑oxo‑2‑(phenylimino)thiazolidin‑5‑ylidene)methyl)‑6‑bromoquinolin‑2(1H)‑one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With sodium acetate; acetic acid for 10h; Reflux; General procedure for the synthesis of (8a-o) General procedure: To a solution of 7a-c (0.01 moles), substituted 2-chloroquinoline-3-carboxaldehyde 3a-e (0.01 moles) and anhydroussodium acetate (0.025 moles) in glacial acetic acid(20 ml) was refluxed for 10 h. After completion of thereaction, it was cooled to room temperature. Resulting solid was filtered off, washed with water, dried and recrystallizedfrom N, N-dimethyl formamide.
  • 46
  • (Z)-3‑(4‑fluorobenzyl)‑2‑(phenylimino)thiazolidin‑4‑one [ No CAS ]
  • [ 73568-35-1 ]
  • 3‑(Z‑(Z‑3‑(4‑fluorophenyl)‑4‑oxo‑2‑(phenylimino)thiazolidin‑5‑ylidene)methyl)‑6‑bromoquinolin‑2(1H)‑one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium acetate; acetic acid for 10h; Reflux; General procedure for the synthesis of (8a-o) General procedure: To a solution of 7a-c (0.01 moles), substituted 2-chloroquinoline-3-carboxaldehyde 3a-e (0.01 moles) and anhydroussodium acetate (0.025 moles) in glacial acetic acid(20 ml) was refluxed for 10 h. After completion of thereaction, it was cooled to room temperature. Resulting solid was filtered off, washed with water, dried and recrystallizedfrom N, N-dimethyl formamide.
  • 47
  • [ 73568-35-1 ]
  • 6-bromoisothiazolo[5,4-b]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With sulfur; ammonium sulfate; potassium phosphate In dimethyl sulfoxide at 100℃; for 15h; 11 Example 11 Combine 6-bromo-2-chloroquinoline-3-carbaldehyde (41.1 mg, 0.2 mmol), S8 (0.1 mmol, 25.6 mg), potassium phosphate (0.3 mmol, 63.7 mg) and ammonium sulfate (0.2 mmol, 26.4 mg), DMSO (0.5 mL) was placed in a hot bath at a set temperature and stirred magnetically. After the reaction is complete, cool to room temperature, wash the reaction mixture with saturated sodium carbonate solution, and extract with CH2Cl2 (10 mL×3), then wash the organic layer with saturated brine, then dry the organic layer with anhydrous sodium sulfate, and filter After that, the solution was concentrated under reduced pressure, and the obtained crude product was separated by thin layer chromatography (TLC), and finally the pure product-6-bromoisothiazolo[5,4-b]quinoline was obtained. White solid, the yield is 61%.
  • 48
  • [ 584-26-9 ]
  • [ 73568-35-1 ]
  • 5-(((6-bromo-quinolin-2-(1H)-one)-3-yl)-methylene)-2-sulfanylideneimidazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; acetic acid Reflux; 3.1.1. General Procedure for the Condensation of 1-acetyl-2-thiohydantoin and 2-thiohydantoin-3-acetic acid with 2-chloro-3-quinolinecarboxaldehyde Derivatives General procedure: The synthesis of 1-acetyl-2-thiohydantoin and 2-thiohydantoin-3-acetic acid, used at subsequent synthetic stages, was published earlier [2]. To a solution of 1-acetyl-2-thiohydantoin(0.791 g, 5 mmol) (1) (Scheme 1, in Results and Discussion) or of 2-thiohydantoin-3-acetic acid (0.871 g, 5 mmol) (2) (Scheme 2, in Results and Discussion) in glacial acetic acid (50 mL), anhydrous sodium acetate was added (1.231 g, 15 mmol, 3 eq.). Then the appropriate 2-chloro-3-quinolincarbaldehyde (5 mmol) was added to the resulting solution.The reaction mixture was heated within 5-6 h under reflux. In the next step the content of the flask was poured into cold water (100 cm3) and the obtained product was filtered off. Finally, the product was crystallized from either glacial acetic acid or acetic anhydride.As a result of the condensation reaction two series of compounds were obtained(Figure 3, Schemes 1 and 2).
  • 49
  • [ 119681-50-4 ]
  • [ 73568-35-1 ]
  • 2-(5-((6-bromo-quinolin-2-(1H)-one)-3-yl)-methylene)-(4-oxo-2-sulfanylideneimidazolidin-3-yl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; acetic acid Reflux; 3.1.1. General Procedure for the Condensation of 1-acetyl-2-thiohydantoin and 2-thiohydantoin-3-acetic acid with 2-chloro-3-quinolinecarboxaldehyde Derivatives General procedure: The synthesis of 1-acetyl-2-thiohydantoin and 2-thiohydantoin-3-acetic acid, used at subsequent synthetic stages, was published earlier [2]. To a solution of 1-acetyl-2-thiohydantoin(0.791 g, 5 mmol) (1) (Scheme 1, in Results and Discussion) or of 2-thiohydantoin-3-acetic acid (0.871 g, 5 mmol) (2) (Scheme 2, in Results and Discussion) in glacial acetic acid (50 mL), anhydrous sodium acetate was added (1.231 g, 15 mmol, 3 eq.). Then the appropriate 2-chloro-3-quinolincarbaldehyde (5 mmol) was added to the resulting solution.The reaction mixture was heated within 5-6 h under reflux. In the next step the content of the flask was poured into cold water (100 cm3) and the obtained product was filtered off. Finally, the product was crystallized from either glacial acetic acid or acetic anhydride.As a result of the condensation reaction two series of compounds were obtained(Figure 3, Schemes 1 and 2).
  • 50
  • [ 934-32-7 ]
  • [ 73568-35-1 ]
  • [ 109-77-3 ]
  • 2-amino-4-(6-bromo-2-chloroquinolin-3-yl)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With ammonium acetate In ethanol for 0.5h; Sonication; General procedure for the synthesis of 2-amino-4-(substituted quinoline)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carbonitriles (TF-1 to TF-8)Ultrasonic-irradiation (US) method General procedure: Take a mixture of 2-aminobenzimidazole (2.0 mmol), malononitrile (2.0 mmol) and 2-chloroquinoline-3-carbaldehyde (2.0 mmol) in EtOH (10 mL) with ammonium acetate in a catalytic amount. The reaction mass was placed in the ultrasound and irradiated with 100 W radiation for 30 min. After completing the reaction (checked by TLC), the resulting solution was cooled to room temperature. Filtered the solid formed and washed with water. The crude product was recrystallized from 95% EtOH to give a pure solid product. (TF-1 to TF-8); yield (80%-94%)
  • 51
  • [ 73568-35-1 ]
  • C10H5BrN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Caswell No. 744A; glacial acetic acid In water monomer; dimethyl sulfoxide at 40℃; 2.3.2. General procedure for synthesis of TQ (1-3) derivatives General procedure: Q (1-3) (0.005 M) in DMSO (20 mL) was taken in round bot- tom flask; add sodium azide (0.015 M) in water (2.5 mL). To this, 0.8 mL of acetic acid was added and mild heat 40 °C was given to the reaction and reaction mixture was kept overnight with stir- ring. The mixture was poured onto crushed ice, filtered and dried. The compounds were purified using column chromatography (n- hexane: ethyl acetate, 6.5:3.5 v/v).
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