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Product Details of [ 33757-42-5 ]

CAS No. :33757-42-5 MDL No. :MFCD00264921
Formula : C11H10N2O Boiling Point : -
Linear Structure Formula :C9H6N(NHCOCH3) InChI Key :YBWWRMMAWZGAPQ-UHFFFAOYSA-N
M.W : 186.21 Pubchem ID :36591
Synonyms :

Safety of [ 33757-42-5 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 33757-42-5 ]

* 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 [ 33757-42-5 ]

[ 33757-42-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 578-66-5 ]
  • [ 75-36-5 ]
  • [ 33757-42-5 ]
YieldReaction ConditionsOperation in experiment
57% With dmap; triethylamine In toluene at 20℃; for 18h; Darkness; 4.2.7. N-Mono(8-quinolyl)acetamide (5). 8-Aminoquinoline (2.7 g) was dissolved in dry toluene (200 mL). Triethylamine (4.0 mL) and N,N'-dimethyl-4-aminopyridine (DMAP) (0.35 g) were added to the solution. In a dark room, the dry toluene solution (40 mL) of acetyl chloride (2.10 g) was added dropwise to the solution and stirred for 18 h at room temperature. After filtration for the removal of the solid, the solution was washed by water (1005 mL). The organic layer was completely evaporated under reduced pressure. Yield: 1.94 g, 57%; pale yellow solid; mp 94.2e96.6 C. IR (KBr):1666.4 cm1. 1H NMR (300 MHz NMR, CDCl3): 2.35 (s, 3H), 7.43 (dd,1H, J4.20 and 8.40 Hz), 7.47 (dd, 1H, J1.80 and 8.40 Hz), 7.52 (dd, 1H, J8.10 and 8.10 Hz), 8.13 (dd, 1H, J1.50 and 8.40 Hz), 8.77 (dd,1H, J1.80 and 8.10 Hz), 8.78 (dd, 2H, J1.50 and 4.20 Hz), 9.78 (br,1H). 13C NMR (75 MHz NMR, CDCl3): 25.3, 116.4, 121.4, 121.6, 127.4,127.9, 134.5, 136.4, 138.2, 148.1, 168.8. HRMS (EI): m/z calcd forC11H10N2O 186.0793, found 186.0797.
32% With pyridine at 20℃;
With triethylamine In dichloromethane at 0 - 20℃;
Stage #1: 8-amino quinoline With triethylamine In dichloromethane for 0.333333h; Stage #2: acetyl chloride In dichloromethane at 0 - 20℃; for 3h;
With triethylamine In ethyl acetate at 0 - 25℃;
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Schlenk technique;
Stage #1: 8-amino quinoline With triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: acetyl chloride In dichloromethane at 20℃; for 12h;
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
With triethylamine In dichloromethane at 0 - 25℃; for 10h;
Stage #1: 8-amino quinoline With triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: acetyl chloride In dichloromethane Cooling with ice; 3.2. Synthesis of Starting Materials General procedure: To a 50 mL single neck flask charged with CH2Cl2 (20 mL) was added 8-aminoquinoline (10mmol) and triethylamine (11 mmol) and stirred at room temperature for 5 min, then the reactionsolution was cooled in an ice bath. The acid chloride (12 mmol) was added dropwise (if solid, it wasdissolved with CH2Cl2). The reaction solution was stirred overnight. When it was completedmonitored by TLC, the mixture was filtered through a pad of Celite, the solid was washed with ethylacetate (30 mL), and the organic layer was washed with 1 M NaHCO3 of aqueous solution (3 × 15mL), then the organic layer was dried with Na2SO4, filtered, and the solvent was removed underreduced pressure. The product was finally obtained by column chromatography on silica (PE/EtOAc = 20/1).
With triethylamine In dichloromethane at 20℃; 4.2 General procedure for synthesis of starting amides General procedure: The synthesis of starting amides was according to previously reported literature. 5 mmol of 8-aminoquinoline, and 6 mmol of triethylamine were dissolved in 20 mL of CH2Cl2, stirred in 100 mL single neck flask at room temperature for 5 minutes, the reaction solution was cooled in an ice bath afterwards. The acid chloride (6 mmol) was added dropwise (if the acid chloride is solid, it was dissolved with 5 mL CH2Cl2). The reaction solution was allowed to stir overnight at room temperature. The reaction mixture was washed with CH2Cl2, and the organic layer with 1M NaHCO3 (3×15 mL). The organic layer was dried over anhydrous Na2SO4, subsequently. The solvent was removed over rotary evaporator. The product was purified by silica gel column chromatography with PE/EtOAc (10 : 1). The synthesis of N-methyl-N-(quinolin-8-yl)benzamide was according to previously reported literature. To a suspension of sodium hydride (2.0 mmol) in 5 mL of dry dimethylformamide, was added a solution of N-8-quinolinyl-benzamide (1.0 mmol) in 5 mL of dry dimethylformamide in an ice bath. The reaction was warmed to room temperature and stirred for another hour. Methyl iodide (1.0 mmol) was added and the reaction mixture was stirred for a further half hour, subsequently. Then the reaction mixture was washed with 30 mL of CH2Cl2 and the organic layer was washed with water (3×15 mL). The organic layer was dried over anhydrous Na2SO4, and the solvent removed roto-evaporated. The product was purified by column chromatography using CH2Cl2 as eluent.
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; (a) General procedure for synthesis of 8-acylamino quinolines [1] General procedure: A mixture of 8-aminoquinoline (1.44g, 10 mmol) and triethylamine (15.0 mmol) was dissolvedin dichloromethane (20 mL) and stirred under 0 . The corresponding acid chloride (11mmol),dissolved in 10mL dichloromethane, was added by dropping funnel over 15 min. Then the mixtu rewas warmed to room temperature and stirred overnight. The reaction mixture was quenched withwater (30 mL) and extracted with CH2Cl2 (10 mL) for three times. The organic layer was dried overMgSO4 and the solvent was removed under reduced pressure. The crude product was purified bychromatography on a silica gel column to afford the 8-acylamino quinolines 1 (5%→30% ethylacetate/hexane).
With triethylamine In dichloromethane at 0 - 20℃; for 10h;
With triethylamine In dichloromethane at 0 - 20℃; for 2h;
With triethylamine In dichloromethane at 0 - 20℃; for 2h;
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;

Reference: [1]Moriuchi-Kawakami, Takayo; Kawata, Keita; Nakamura, Sho; Koyama, Yoshiaki; Shibutani, Yasuhiko [Tetrahedron, 2014, vol. 70, # 52, p. 9805 - 9813]
[2]Perez, Christian; Barkley-Levenson, Amanda M.; Dick, Benjamin L.; Glatt, Peter F.; Martinez, Yadira; Siegel, Dionicio; Momper, Jeremiah D.; Palmer, Abraham A.; Cohen, Seth M. [Journal of Medicinal Chemistry, 2019, vol. 62, # 3, p. 1609 - 1625]
[3]Zhu, Longzhi; Qiu, Renhua; Cao, Xin; Xiao, Song; Xu, Xinhua; Au, Chak-Tong; Yin, Shuang-Feng [Organic Letters, 2015, vol. 17, # 22, p. 5528 - 5531]
[4]Wang, Ying; Wang, Yang; Jiang, Kai; Zhang, Qian; Li, Dong [Organic and Biomolecular Chemistry, 2016, vol. 14, # 43, p. 10180 - 10184]
[5]Huang, Binbin; Zhao, Yating; Yang, Chao; Gao, Yuan; Xia, Wujiong [Organic Letters, 2017, vol. 19, # 14, p. 3799 - 3802]
[6]Li, You; Zhu, Longzhi; Cao, Xin; Au, Chak-Tong; Qiu, Renhua; Yin, Shuang-Feng [Advanced Synthesis and Catalysis, 2017, vol. 359, # 16, p. 2864 - 2873]
[7]Vinayak, Botla; Navyasree, Pilli; Chandrasekharam, Malapaka [Organic and Biomolecular Chemistry, 2017, vol. 15, # 43, p. 9200 - 9208]
[8]Samanta, Supravat; Ravi, Chitrakar; Rao, Sadu Nageswara; Joshi, Abhisek; Adimurthy, Subbarayappa [Organic and Biomolecular Chemistry, 2017, vol. 15, # 45, p. 9590 - 9594]
[9]Zhang, Yingchao; Wen, Chunxia; Li, Jizhen [Organic and Biomolecular Chemistry, 2018, vol. 16, # 11, p. 1912 - 1920]
[10]Long, Yang; Pan, Lei; Zhou, Xiangge [Molecules, 2019, vol. 24, # 3]
[11]Shu, Quan; Li, Yaming; Liu, Tong; Zhang, Siyu; Jiang, Linlin; Jin, Kun; Zhang, Rong; Duan, Chunying [Tetrahedron, 2019, vol. 75, # 26, p. 3636 - 3642]
[12]Aisha, Aertuke; Jin, Can; Li, Deyu; Sun, Bin; Zhu, Rui; Zhuang, Xiaohui [Synlett, 2020, vol. 31, # 7, p. 677 - 682]
[13]Wen, Chunxia; Zhong, Ronglin; Qin, Zengxin; Zhao, Mengfei; Li, Jizhen [Chemical Communications, 2020, vol. 56, # 66, p. 9529 - 9532]
[14]Chen, Meng-Yi; Fang, Zheng; Guo, Kai; Lin, Xin-Xin; Liu, Cheng-Kou [Green Chemistry, 2020, vol. 22, # 19, p. 6437 - 6443]
[15]Lin, Xinxin; Zeng, Cuilian; Liu, Chengkou; Fang, Zheng; Guo, Kai [Organic and Biomolecular Chemistry, 2021, vol. 19, # 6, p. 1352 - 1357]
[16]Liu, Feng; Wu, Na; Cheng, Xu [Organic Letters, 2021, vol. 23, # 8, p. 3015 - 3020]
  • 2
  • [ 33757-42-5 ]
  • [ 5335-87-5 ]
  • N-(5-((4-methoxyphenyl)thio)quinolin-8-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With oxygen; copper(ll) bromide In N,N-dimethyl-formamide at 160℃; for 24h; Schlenk technique; regioselective reaction;
80% With oxygen; copper(ll) bromide In N,N-dimethyl-formamide at 160℃; for 24h; 18 Preparation Example 18 Add 0.25 mmol of 8-acetamidoquinoline (R1=CH3), 0.3 mmol of p-methoxyphenyl disulfide (R2=p-MeO-Ph), CuBr2 0.5 mmol, and 1 mL of DMF to a 10 mL reaction tube. The reaction was carried out at 160 ° C for 24 h under an oxygen atmosphere. After completion of the reaction, filtration, concentration and separation by column chromatography gave 5-(4-methoxyphenylmercapto)-8-acetamidoquinoline in a yield of 80%.
  • 3
  • [ 33757-42-5 ]
  • [ 2618-96-4 ]
  • N-(5-(N-(phenylsulfonyl)phenylsulfonamido)quinolin-8-yl)acetamide [ No CAS ]
  • 4
  • [ 33757-42-5 ]
  • [ 99851-80-6 ]
YieldReaction ConditionsOperation in experiment
98% With N-benzyl-N,N,N-triethylammonium chloride; N,N'-dibromohydantoin In water at 20℃; for 12h; 2; 21; 22 Example 22 This example is the amplification reaction of Example 2. The preparation method of an 8-amide-5-haloquinoline derivative of the present invention is used to prepare N-(5-bromoquinolin-8-yl)acetamide (1ab ), the English name is N-(5-bromoquinolin-8-yl)acetamide(1ab), and its chemical reaction formula is as follows:The specific steps are as follows: Put 8-acetylaminoquinoline (1.86g, 0.01mol), dibromohydantoin (1.43g, 0.05mol), TEBA (0.45g, 0.002mol) and 100mL of water into a 250mL reaction flask, at room temperature The reaction was stirred for 12 hours, and 2.6 g of white solid (target compound I, 1ab) was obtained after filtration, with a yield of 98% (calculated as 8-acetamidoquinoline).
97% With Eosin Y; Selectfluor In acetonitrile at 25℃; for 1h; regioselective reaction;
96% With 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione In acetonitrile at 20℃; for 0.5h; regioselective reaction;
95% With N-Bromosuccinimide; (Z)-N-[3,5-bis(trifluoromethyl)phenyl]-4-(dimethyliminio)pyridine-1(4H)-carbimidothioate In dichloromethane at 25℃; for 36h; Darkness; regioselective reaction;
95% With N-Bromosuccinimide In acetonitrile for 2h; Irradiation; regioselective reaction;
94% With Iron(III) nitrate nonahydrate; N-Bromosuccinimide; oenanthic acid; sodium hydrogencarbonate In water at 20℃; for 24h; Schlenk technique; Green chemistry; regioselective reaction; 3.3. General Procedures for Iron-Catalyzed Halogenation C5-H of 8-Amidoquinolines under Mild Conditionsin Water General procedure: Reaction conditions A: A mixture of 1 (0.3 mmol), NBS (0.6 mmol), Fe(NO3)3*9H2O(5 mol%),CH3(CH2)5COOH (0.3 mmol), NaHCO3 (0.3 mmol) in water (1.0 mL) in a 20 mL Schlenktube was stirred at room temperature for 24 h. Then, the mixture was extracted with EtOAc (10 mL 4). The combined organic layer was dried with Na2SO4 and filtered through a pad ofCelite. The solvent was removed under reduced pressure and the residue was purified by silica gelcolumn chromatography using PE/EtOAc (20/1) as an eluent to afford the products.
88% With oxone; sodium bromide In 1,2-dichloro-ethane at 25℃; for 10h; Sealed tube;
82% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In dichloromethane at 20℃; for 0.5h; Irradiation; regioselective reaction; 4.4 General procedure for the synthesis of brominated quinolines in continuous flow General procedure: 0.2 mmol of substituted quinolines and 0.11mmol of DBDMH in CH2Cl2 (2mL) was injected into the pump, then the reaction mixture entered into the fluorinated ethylene propylene (FEP) tubing convection flow coil reactor (1/32 inner diameter, 1.6mL inner volume, 53.3 μLmin-1 flow rate), which was maintained at room temperature (residence time=30min) and under the irradiation of blue-LED. The reaction mixture was collected at a test tube and then concentrated under vacuum. The residue was purified by column chromatography on silica gel (200-300 mesh) with PE/EtOAc (10 : 1) to give the final products.
75% With dipotassium peroxodisulfate; lithium bromide In acetonitrile at 80℃; for 8h; Inert atmosphere; General Procedure for 5-Halogenation of N-(quinolin-8-yl)benzamide. General procedure: A mixture of N-(quinolin-8-yl)benzamide (0.2 mmol, 49.6 mg, 1.0 equiv), LiX (0.3 mmol, 1.5equiv, X = Cl, Br, I), and K2S2O8 (108 mg, 0.4 mmol, 2 equiv for chlorination and bromination;162 mg, 0.6 mmol, 3 equiv for iodination) in MeCN was stirred under argon at 80 °C (100 °C, X =I) for 8 h followed by cooling to room tempareture. The solvent removed under reduced pressure.The contents were subjected to flash chromatography to give the corresponding product as whitesolids (X = Cl, 0.16 mmol, 43.4 mg, 82%; X = Br, 0.19 mmol, 58.9 mg, 95%; X = I, 0.17 mmol,63.6 mg, 85%). The purified material was dried under an oil-pump vacuum.
71% With bis-[(trifluoroacetoxy)iodo]benzene; sodium bromide In ethanol at 25℃; for 0.166667h; Green chemistry; regioselective reaction;
With N-Bromosuccinimide In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Schlenk technique;
With N-Bromosuccinimide In toluene at 50℃; for 18h; Inert atmosphere; 2 Preparation 2 To a 10 mL reaction tube was added 0.2 mmol of 8- (acetylamino) quinoline (R1 = Me)0.22 mmol of NBS and 1 mL of toluene under a nitrogen atmosphere,The reaction was carried out at 50 ° C for 18 h.After completion of the reaction, the reaction is cooled to room temperature,Then, 0.3 mmol of styrene was added under a nitrogen atmosphere,0.4 mmol of sodium carbonate and 0.02 mmol of catalyst bis (tris (2-methyl) phenyl) phosphine dichloride were placed in the reaction vessel,1 mL of DMSO was added to the solvent, reacted at 50 ° C for 12 hours,After completion of the reaction, the residue was filtered and concentrated, and 5-styryl-8- (acetylamino) quinoline was separated by column chromatography in a yield of 85%.
With bromine In N,N-dimethyl-formamide at 160℃; for 6h; Inert atmosphere; 18 Preparation Example 18 To a 10 mL reaction tube was added 0.2 mmol of 8- (acetyl) aminoquinoline, 0.22 mmol of Br2 and 1 mL of DMF, The reaction was carried out at 160 ° C for 6 h. After completion of the reaction, the reaction was allowed to cool to room temperature and then added under a nitrogen atmosphere0.3 mmol of 4-tert-butylphenylacetylene, 2 mmol of triethylamine, 0.04 mmol of nickel acetate and 0.002 mmol of copper bromide, 1 mL of DMF,50 ° C for 12 hours. After the reaction, the reaction mixture was filtered, concentrated and separated by column chromatography5- (4-tert-butylphenethynyl) -8- (acetyl) aminoquinoline in 80% yield.

Reference: [1]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN111320579, 2020, A Location in patent: Paragraph 0026-0031; 0130-0137
[2]Huang, Binbin; Zhao, Yating; Yang, Chao; Gao, Yuan; Xia, Wujiong [Organic Letters, 2017, vol. 19, # 14, p. 3799 - 3802]
[3]Motati, Damoder Reddy; Uredi, Dilipkumar; Watkins, E. Blake [Chemical Science, 2018, vol. 9, # 7, p. 1782 - 1788]
[4]Xiong, Xiaodong; Tan, Fei; Yeung, Ying-Yeung [Organic Letters, 2017, vol. 19, # 16, p. 4243 - 4246]
[5]Singh, Harshvardhan; Sen, Chiranjit; Sahoo, Tapan; Ghosh, Subhash Chandra [European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4748 - 4753]
[6]Long, Yang; Pan, Lei; Zhou, Xiangge [Molecules, 2019, vol. 24, # 3]
[7]Wang, Ying; Wang, Yang; Jiang, Kai; Zhang, Qian; Li, Dong [Organic and Biomolecular Chemistry, 2016, vol. 14, # 43, p. 10180 - 10184]
[8]Shu, Quan; Li, Yaming; Liu, Tong; Zhang, Siyu; Jiang, Linlin; Jin, Kun; Zhang, Rong; Duan, Chunying [Tetrahedron, 2019, vol. 75, # 26, p. 3636 - 3642]
[9]Chen, Xiang-Xiang; Wang, Jia-Xin; Ren, Jiang-Tao; Xie, Hu; Zhao, Yanxia; Li, Ya-Min; Sun, Meng [Synlett, 2017, vol. 28, # 14, p. 1840 - 1844]
[10]Tian, Chao; Yao, Xu; Ji, Weizhe; Wang, Qian; An, Guanghui; Li, Guangming [European Journal of Organic Chemistry, 2018, vol. 2018, # 43, p. 5972 - 5979]
[11]Li, You; Zhu, Longzhi; Cao, Xin; Au, Chak-Tong; Qiu, Renhua; Yin, Shuang-Feng [Advanced Synthesis and Catalysis, 2017, vol. 359, # 16, p. 2864 - 2873]
[12]Current Patent Assignee: HUNAN UNIVERSITY - CN106938985, 2017, A Location in patent: Paragraph 0022; 0023
[13]Current Patent Assignee: HUNAN UNIVERSITY - CN106905233, 2017, A Location in patent: Paragraph 0055; 0056; 0059; 0060
  • 5
  • [ 33757-42-5 ]
  • [ 683-98-7 ]
  • methyl 2-(8-acetamidoquinolin-5-yl)-2,2-difluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; potassium hydrogencarbonate In 1,4-dioxane at 150℃; for 12h; Schlenk technique; regioselective reaction;
  • 6
  • [ 33757-42-5 ]
  • [ 14062-05-6 ]
  • 5-(4-methylbenzenesulfonyloxy)-8-acetamidoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; at 20℃; for 1h; A 250 mL four-necked flask was charged with tetrahydrofuran (100 mL), 8-acetamidoquinoline (II-1) (1,86 g, 0.01 mol), N, Hydrazine (III-1) (3.70 g, 0.01 mol) and iodobenzene trifluoroacetate (14.2 g, 0.033 mol) were added and the mixture was stirred at room temperature for 1 hour. The mixture was filtered and the filter cake was washed with methylene chloride. Column chromatography (petroleum ether / ethyl acetate as eluent, gradient elution) gave 2.78 g of a white solid in 78% yield
53% With bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; at 20℃; for 3h; A 250 mL four-necked flask was charged with tetrahydrofuran (100 mL), 8-acetamidoquinoline (II-1) (1,86 g, 0.01 mol), N,N'-bis (4-methylphenylsulfonyl) hydrazine (III-1) (1.85g, 0.005mol) and iodobenzene trifluoroacetate (5.32g, 0.017mol) were added and the mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered and the solvent was removed under reduced pressure to give a crude product. Ethyl acetate as eluent, gradient elution) to give a white solid 1.89g, 53% yield.
  • 7
  • [ 578-66-5 ]
  • [ 64-19-7 ]
  • [ 33757-42-5 ]
YieldReaction ConditionsOperation in experiment
79% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; N-(Quinolin-8-yl)benzamides 1; General Procedure General procedure: To a solution of the respective carboxylic acid (6 mmol), the corresponding 8-aminoquinoline (6 mmol), and DMAP (73 mg, 0.6 mmol)in anhyd CH2Cl2 (30 mL) was added a solution of EDCI (1.38 g, 7.2mmol) in CH2Cl2 (30 mL) through a dropping funnel at 0 °C under N2 atmosphere. The mixture was allowed to stir at r.t. for overnight. After completion, the mixture was diluted with CH2Cl2 (50 mL). The organic layer was washed with aq 1N HCl (15 mL), followed by aq NaHCO3 (15mL), brine (25 mL), and dried (NaSO4). The organic solvent was removed by evaporation and the residue was purified by column chromatography using EtOAc/hexane to afford the desired pure N-(quino-lin-8-yl)arylamide 1.
Stage #1: acetic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 5h; Stage #2: 8-amino quinoline With triethylamine In dichloromethane at 0 - 20℃; Synthesis of N-(quinolin-8-yl)benzamides General procedure: To an oven-dried round bottom flask (100 mL) charged with a magnetic stir-bar was added benzoic acid (10 mmol), DMF (50 μL) and DCM (30mL). Oxalyl chloride (20 mmol, 1.8 mL) was added dropwise under ice cold condition. The ice bath was removed and the reaction mixture was stirred at room temperature for 5 h. The solvent was then removed by evaporation under reduced pressure, and the resulting residue was dissolved in CH2Cl2 (15 mL). After cooling the reaction mixture to 0 °C, another oven-dried round bottom flask (100 mL) charged with a magnetic stir-bar was added 8-aminoquinoline (10 mmol, 1.44 g), Et3N (20 mmol, 2.8 mL) and DCM (30 mL). To this, a solution of acid chloride in DCM was added dropwise under ice cold condition and was stirred overnight under room temperature. Then, it was treated with water, and extracted with DCM (3 x 10 mL). The combined organic phase was dried over anhydrous Na2SO4 and the solvent is removed by evaporation under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: EtOAc/PE) to give the desired amides.
  • 8
  • [ 33757-42-5 ]
  • [ 14062-05-6 ]
  • C18H16N2O3(18)OS [ No CAS ]
  • 9
  • [ 33757-42-5 ]
  • [ 401-55-8 ]
  • ethyl 2-(8-acetamidoquinolin-5-yl)-2-fluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With 4,4'-dimethyl-2,2'-bipyridines; sodium carbonate; copper(II) sulfate; Dimethyl phosphite In 1,2-dichloro-ethane at 110℃; for 24h; Schlenk technique; Sealed tube; 4. General procedure for the reaction General procedure: A dried 25 mL Schlenk tube equipped with a magnetic stir bar was charged with 1 (0.3 mmol, 1.0 equiv), CuSO4 (0.03 mmol, 10 mol%), L3 (Bpy) (0.03 mmol, 10 mol%), Na2CO3 (0.6 mmol, 2.0 equiv) and (CH3O)2P(O)H (0.15 mmol, 50 mol%), 2 (0.9 mmol, 3.0 equiv), DCE (1.5 mL). Subsequently, the tube was sealed and the resulting mixture was stirred at 110 °C for 24 h. After cooling to room temperature, the yield of standard reaction were obtained by HPLC. The crude production was diluted with CH2Cl2 and H2O, and then the resulting mixture was filtered through a pad of Celite. The filtrate was extracted with CH2Cl2 (3 × 10 mL). After the eluent had been concentrated under vacuum, the residue was purified by silica gel plates to give the pure products. The products were characterized by 1H NMR, 13C NMR, LC-MS.
  • 10
  • [ 33757-42-5 ]
  • [ 84379-72-6 ]
  • N-(2-(tert-butyl)quinolin-8-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique; C. General procedure for the synthesis of 3(3aa as an example) General procedure: To a 10 mL Schlenk-tube was charged with N-(quinolin-8-yl)benzamide 1a (124 mg, 0.5 mmol),tert-butyl NHP ester 2a (247 mg, 1.0 mmol), fac-Ir(ppy)3 (6 mg, 0.01 mmol), trifluoroacetic acid(29 mg, 0.25 mmol) and DMSO (3.0 mL). The tube was evacuated and backfilled with N2 for threetimes. The mixture was then irradiated with 3W white CFL lamps and stirred for 12 hours at roomtemperature. After the reaction finished, the reaction mixture was quenched with water (10 mL) andextracted with DCM (10 mL). The organic layer was dried over Na2SO4 and concentrated underreduced pressure. The crude product was purified by flash chromatography on silica gel column(ethyl acetate/hexane, 1:200) to afford 3aa (123 mg, 81%) as a white solid.
  • 11
  • [ 33757-42-5 ]
  • [ 1631179-23-1 ]
  • [ 2410649-92-0 ]
YieldReaction ConditionsOperation in experiment
81% With fac-tris(2-phenylpyridinato-N,C2')iridium(III); trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique; C. General procedure for the synthesis of 3(3aa as an example) General procedure: To a 10 mL Schlenk-tube was charged with N-(quinolin-8-yl)benzamide 1a (124 mg, 0.5 mmol),tert-butyl NHP ester 2a (247 mg, 1.0 mmol), fac-Ir(ppy)3 (6 mg, 0.01 mmol), trifluoroacetic acid(29 mg, 0.25 mmol) and DMSO (3.0 mL). The tube was evacuated and backfilled with N2 for threetimes. The mixture was then irradiated with 3W white CFL lamps and stirred for 12 hours at roomtemperature. After the reaction finished, the reaction mixture was quenched with water (10 mL) andextracted with DCM (10 mL). The organic layer was dried over Na2SO4 and concentrated underreduced pressure. The crude product was purified by flash chromatography on silica gel column(ethyl acetate/hexane, 1:200) to afford 3aa (123 mg, 81%) as a white solid.
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