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[ CAS No. 613-30-9 ] {[proInfo.proName]}

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Chemical Structure| 613-30-9
Chemical Structure| 613-30-9
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Product Details of [ 613-30-9 ]

CAS No. :613-30-9 MDL No. :MFCD00051736
Formula : C10H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DXDPHHQJZWWAEH-UHFFFAOYSA-N
M.W : 188.18 Pubchem ID :69172
Synonyms :

Calculated chemistry of [ 613-30-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.53
TPSA : 58.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 2.42
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 0.96
Log Po/w (SILICOS-IT) : 0.7
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.191 mg/ml ; 0.00101 mol/l
Class : Soluble
Log S (Ali) : -3.3
Solubility : 0.0953 mg/ml ; 0.000507 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.47
Solubility : 0.0638 mg/ml ; 0.000339 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 613-30-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 613-30-9 ]

* 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 [ 613-30-9 ]

[ 613-30-9 ] Synthesis Path-Downstream   1~85

  • 1
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  • 3
  • [ 78267-54-6 ]
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  • 4
  • [ 56008-61-8 ]
  • furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
  • [ 67-64-1 ]
  • [ 613-30-9 ]
  • 5
  • [ 56008-61-8 ]
  • [ 67-64-1 ]
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  • 6
  • [ 555-16-8 ]
  • [ 613-30-9 ]
  • 6-nitro-2-(4-nitro-<i>trans</i>-styryl)-quinoline [ No CAS ]
  • 7
  • [ 100-52-7 ]
  • [ 5435-44-9 ]
  • [ 613-30-9 ]
  • [ 119062-64-5 ]
  • 9
  • [ 100-10-7 ]
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  • <i>N</i>,<i>N</i>-dimethyl-4-[<i>trans</i>(?)-2-(6-nitro-[2]quinolyl)-vinyl]-aniline [ No CAS ]
  • 10
  • [ 613-30-9 ]
  • [ 65079-19-8 ]
YieldReaction ConditionsOperation in experiment
86.43% With hydrogenchloride; tin(ll) chloride; In ethanol; water; for 5h;Reflux; The above <strong>[613-30-9]2-methyl-6-nitroquinoline</strong> (500 mg, 2.66 mmol) was taken in an eggplant-shaped flask.Add ethanol to dissolve, and add 9M hydrochloric acid (20ml) to the reaction flask.Then, a solution of stannous chloride (2.02 g, 10.63 mmol) in ethanol was added dropwise.After the dropwise addition, the reaction solution was heated to reflux for 5 hours, cooled to room temperature; and the ethanol was removed.The remaining solution was adjusted to pH 9 with sodium hydroxide solids in an ice bath.The milky white emulsion was extracted five times with ethyl acetate and the organic phases were combined.Add diatomaceous earth and stir overnight, and filter the next day.The filtrate was spun dry to give a white solid.Intermediate 2-methyl-6-aminoquinoline(363.29 mg, yield 86.43%).
80% With hydrogenchloride; tin(ll) chloride; In water; for 0.333333h;Reflux; j00230J To a solution of <strong>[613-30-9]2-methyl-6-nitroquinoline</strong> (500 mg, 2.7 mmol) in iN HC1 (20 mL) was added a solution of SnC12 (2.5 g, 13 mmol) in iN HC1 (10 mL) at RT. The resulting reaction mixture was reflux for 20 mm and then cooled to RT. To the solution was added NaHCO3 slowly until pH = 10, and then extracted with DCM. The organic layer was washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4, concentrated, and purified on silica gel flash chromatography (DCM : MeOH = 15 : 1), giving the El (336 mg, 80% yield).
74.2% With hydrogenchloride; tin(ll) chloride; at 105℃; A mixture of compound 2 (16.4 g, 87 mmol) and 1N HCl (70 mL) was heated to 105?, then stannous chloride (100 g, 435 mmol) which was dissolved in 1N HCl (50 mL) was added. Refluxed until the TLC showed that no raw material exists. After cooling to room temperature, 100 mL water was added, then the mixture was extracted by acetic ether (50 mL×3). The water layer was neutralized with ammonia water and then extracted with acetic ether (50 mL×2). The organic phases were combined and dried over Na2SO4. The filtrate was evaporated to generate crude residue, which was recrystallized in ethanol to yield 10.2 g product (65.55 mmol, 74.2%). 1H NMR (400MHz, CDCl3, ppm): 2.68 (3H, s), 3.94 (2H, s), 6.87-6.88 (1H, d, J=2.05 Hz), 7.11-7.14 (1H, dd, J=2.22 Hz, 8.90 Hz), 7.16-7.18 (1H, d, J=8.43 Hz), 7.79-7.82 (1H, d, J=8.44 Hz), 7.84-7.87 (1H, d, J=8.92 Hz). 13C NMR (100MHz, CDCl3,ppm): delta 24.87,107.71, 121.40, 122.25, 127.80, 129.59, 134.17, 142.86, 143.94, 155.08
68.3% Preparation of 2-Methylquinolin-6-amine (2) To a solution of <strong>[613-30-9]2-methyl-6-nitroquinoline</strong> (12 g, 63.84 mmol) in HCl (1N, 450 mL) was added a solution of SnCl2.2H2O (72 g, 0.32 mol) in HCl (1N, 150 mL) slowly. The reaction mixture was heated to reflux for 15 min, then cooled to room temperature. The precipitate was filtered. The filtrate was basified by aqueous KOH and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to give 6.9 g of 2-methylquinolin-6-amine (68.3%). MS [M++1]=159, LC-MS: tR=0.255 min.
palladium-carbon; In ethanol; (A) 6-Amino-2-methylquinoline STR46 2-Methyl-6-nitroquinoline (18.8 g) was stirred under a hydrogen atmosphere at 30 p.s.i. (equivalent to 206. 8 kPa) for 2 hours in ethanol solution containing 5% Pd/C. The catalyst was then removed by filtration, the filtrate evaporated to small volume in vacuo, and the resultant precipitate collected by filtration, washed with ethanol and ether, and dried to give the title compound, yield 13.2 g, m.p. 188-189. Analysis %: Found: C,75.7; H,6.4; N,17.6;
palladium-carbon; In ethanol; (A) 6-Amino-2-methylquinoline STR25 2-Methyl-6-nitroquinoline (18.8 g) was stirred under a hydrogen atmosphere at 206.8 kPa (30 p.s.i.) for 2 hours in ethanol solution containing 5% Pd/C. The catalyst was then removed by filtration, the filtrate evaporated to small volume in vacuo, and the resultant precipitate collected by filtration, washed with ethanol and ether, and dried to give the title compound, yield 13.2 g, m.p. 188-189. Analysis %: Found: C, 75.7; H, 6.4; N, 17.6; Calculated for C10 H10 N2: C, 75.9; H, 6.4; N, 17.7.
With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 2h; General procedure: A mixture of compound 25 (0.4g, 2.1mmol), a catalytic amount of Pd/C, and MeOH (10mL) was stirred under hydrogen at rt for 2h. The reaction was filtered to remove the Pd/C, and then the resulting filtrate was dried under reduced pressure to afford a gray solid. The resulting solid was dissolved in DCM (10mL), and then 4-methoxybenzenesulfonyl chloride (0.48g, 2.3mmol) and pyridine (0.18mL, 2.2mmol) were added and the mixture was stirred for 1h. The reaction mixture was filtered and the filtrate was purified by column chromatography to afford compound 26 (0.39g, 55.9%). 1H NMR (300MHz, CDCl3): delta=2.71 (s,3H), 3.75 (s, 3H), 6.83 (d, J=8.7Hz, 2H), 7.24 (d, J=8.4Hz, 1H), 7.43 (d, J=2.4, 9.0Hz, 1H), 7.57 (d, J=2.1Hz, 1H), 7.75 (d, J=9.0Hz, 2H), 7.88-7.96 (m, 2H).

  • 11
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  • [ 1207-81-4 ]
  • 12
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  • 1-ethyl-2-methyl-6-nitro-quinolinium; iodide [ No CAS ]
  • 13
  • [ 100-01-6 ]
  • [ 123-63-7 ]
  • [ 613-30-9 ]
YieldReaction ConditionsOperation in experiment
33% With hydrogenchloride; In water; at 95℃; for 3.16667h; a. Paraldehyde, 4.5 mL (0.025 mol), was added over a period of 10 min to a solution of 3.2 g (0.022 mol) of p-nitroaniline in 200 mL of concentrated aqueous HCl.The mixture was heated to 95C, stirred for 3 h at that temperature, cooled, poured into 200 mL of water, and neutralized with 20% aqueous potassium hydroxide topH 8. The precipitate was filtered off, washed with a 5% alkali solution, dried, and dissolved in benzene, and the solution was subjected to alumina column chromatography. Elution with chloroform gave 0.22 g(33%) of 2-methyl-6-nitroquinoline (9) (yellow zone),yellow crystals, mp 163-164C [13]. IR spectrum(mineral oil), nu, cm-1: 1600 (C=Carom), 1465 and 1390(NO2). 1H NMR spectrum (CDCl3), delta, ppm: 2.67 s(CH3), 6.38 d and 7.32 d (3-H, 4-H, J = 9 Hz), 7.80-8.56 m (Harom).
  • 14
  • [ 91-63-4 ]
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  • 15
  • [ 186581-53-3 ]
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  • 16
  • [ 110-86-1 ]
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  • [ 66048-83-7 ]
  • 17
  • [ 77-76-9 ]
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  • [ 112089-59-5 ]
  • 18
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  • [ 74-88-4 ]
  • 1,2-Dimethyl-6-nitro-quinolinium; perchlorate [ No CAS ]
  • 19
  • [ 613-30-9 ]
  • [ 76253-89-9 ]
YieldReaction ConditionsOperation in experiment
With m-chloroperoxybenzoic acid; In dichloromethane; Step 1) Preparation of 2-Methyl-6-nitroquinoline N-oxide To a stirring solution of <strong>[613-30-9]2-methyl-6-nitroquinoline</strong> (10.0 g, 53.79 mmol) was added 98% 3-chloroperoxybenzoic acid (11.6 g, 66.10 mmol) in dichloromethane (150 mL). The mixture was stirred at 40 C. overnight, filtered and washed with 10% K2 CO3 to afford 10.03 (92%) of pure N-oxide. 1 H NMR (CDCl3): delta8.94 (d, J=8.90 Hz, 1H, quinoline-H), 8.80 (s, 1H, quinoline-H), 8.49 (d, J=9.22 Hz, 1H, quinoline-H), 7.83 (d, J=9.22 Hz, 1H, quinoline-H), 7.52 (d, J=9.10 Hz, 1H, quinoline-H), 2.57 (s, 3H, CH3).
  • 21
  • [ 100-01-6 ]
  • [ 123-73-9 ]
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YieldReaction ConditionsOperation in experiment
93% With hydrogenchloride; zinc(II) chloride; In water; toluene; at 50℃; for 3h; 150 mL of 30% HCl, 0.01 mol of zinc chloride and 13.8 g (0.1 mol) of 4-nitroaniline were placed in a three-necked flask, and an oil bath was added at 50 C. 0.15 mol of crotonaldehyde (13 mL, dissolved in 100 mL) was slowly added dropwise with stirring. Toluene). After the completion of the dropwise addition, the reaction was continued for 3 hours, cooled, and the organic layer was separated. The aqueous layer was adjusted to pH 3 with Na2CO3, filtered and filtered. The filtrate was then adjusted to pH with Na2CO3 to about 7, filtered and washed with distilled water, and dried to yield 17.5 g of bright yellow. Product, yield 93%.
61% With hydrogenchloride; In tetrahydrofuran; water; at 105℃; A mixture of 4-nitrobenzenamine (29.63 g, 272 mmol), HCl (6N, 100 mL) was heated to 105?,then crotonaldehyde (23 g, 326 mmol) which was dissolved inTHF (90 mL) was added slowly. Refluxed until the TLC showed that no raw materialexists. After cooling to room temperature, 200 mL H2O was added, then the mixture was extracted by acetic ether (100 mL×2). The water layer was neutralized with ammonia water and then extracted with acetic ether (50 mL×2). The organic phases were combined and dried over Na2SO4.The filtrate was evaporated to give crude residue, which was recrystallized in ethanol to yield 31.12 g product (165.9 mmol, 61%). 1H NMR (400MHz, CDCl3,ppm): 2.82 (3H, s), 7.45-7.47 (1H, d, J=8.48 Hz), 8.13-8.15 (1H, d, J=9.23 Hz),8.22-8.25 (1H, d, J=8.48 Hz). 8.43-8.46 (1H, dd, J=9.23 Hz), 8.74-8.75 (1H, d, J=2.07Hz). 13C NMR (100MHz, CDCl3, ppm): delta 24.85?107.71?121.40?122.25?127.81?129.58?134.17?142.86?143.97?155.07.
55.8% With hydrogenchloride; In water; toluene; for 2h;Reflux; Inert atmosphere; General procedure: A mixture of 4-bromoaniline (3.0g, 17.5mmol), crotonaldehyde (1.3g, 18.6mmol), 6N HCl (60mL, 360mmol), and toluene (3mL) was heated to reflux for 2h. The reaction mixture was cooled and neutralized with aqueous NaOH. The resulting mixture was extracted with EtOAc, and then the organic layer was purified by column chromatography to afford compound 17 (0.6g, 15.5%). 1H NMR (300MHz, DMSO-d6): delta=3.33 (s, 3H), 7.44 (d, J=8.4Hz, 1H), 7.76-7.90 (m, 2H), 8.10-8.22 (m, 2H).
  • 22
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  • [ 74-88-4 ]
  • [ 59105-87-2 ]
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  • [ 123-73-9 ]
  • [ 100-01-6 ]
  • [ 613-30-9 ]
YieldReaction ConditionsOperation in experiment
81.2% Preparation of 2-Methyl-6-nitroquinoline (1) 4-Nitroaniline (6 g, 38 mmol) was dissolved in HCl (6N, 200 mL), the mixture was heated at 100 C. A solution of (E)-but-2-enal (7.2 mL, 76 mmol) in toluene (60 mL) was added dropwise, and the reaction was heated at 100 C. overnight. The reaction mixture was cooled to room temperature and basified with aqueous KOH until pH=12. The mixture was extracted with EtOAc and the organic layer was washed with brine and dried over anhydrous Na2SO4. 2-Methyl-6-nitroquinoline was obtained after purification by column chromatography (hexane: EtOAc=20:1) (5.8 g, 81.2%). MS [M++1]=189, LC-MS: tR=1.64 min.
  • 25
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  • [ 59500-67-3 ]
YieldReaction ConditionsOperation in experiment
89% With selenium(IV) oxide; In 1,4-dioxane; water; for 0.5h;Heating / reflux; Step A: 6-nitroquinoline-2-carbaldehyde To a hot solution of selenium dioxide (41.6 g, 375 mmol) in dioxane (185 mL) and water (35 mL) was added <strong>[613-30-9]2-methyl-6-nitroquinoline</strong> (47.0 g, 250 mmol). The mixture was refluxed for 30 minutes. The selenium black was filtered off and the filtrate was concentrated by rotary evaporation. The resulting solid was filtered, washed with a saturated solution of sodium bicarbonate and then water, and dried to give the product as a tan solid (44.8 g, 89%). 1H NMR (300 MHz, DMSO-d6) delta 10.17 (s, 1H), 9.21 (d, J=2.6 Hz, 1H), 8.97 (d, J=8.5 Hz, 1H), 8.59 (dd, J=2.6 Hz, J'=9.2 Hz, 1H), 8.44 (d, J=9.2 Hz, 1H), 8.16 (d, J=8.5 Hz, 1H).
81% With Iron(III) nitrate nonahydrate; In toluene; at 130℃; for 0.166667h;Microwave irradiation; <strong>[613-30-9]2-methyl-6-nitroquinoline</strong> (0.752 g, 4 mmol), Fe (NO) was added to a 80 mL microwave tube,3)3· 9H2(1.616 g, 4 mmol) and toluene (40 mL) were heated to 130 C for 10 min at 150 W in a CEM Discover microwave reactor.After completion of the reaction, the mixture was cooled to room temperature, filtered and the filtrate was poured into saturated NaHCO3Aqueous solution, ethyl acetate (3 x 30 mL), and the combined organic layers were washed with anhydrous Na2SO4After drying, it was concentrated under reduced pressure and recrystallized from n-hexane (30 mL) to give 0.654 g of a yellow target product in 81% yield.
68% With [bis(acetoxy)iodo]benzene; In water; at 105℃; for 0.5h;Microwave irradiation; Sealed tube; Green chemistry; General procedure: Unless otherwise noted, reactions were carried out as following: 2-methylquinolines 1 (2 mmol), PIDA (4 mmol), DMSO(10 mL) were mixed in a sealed microwave tube. The reaction mixture was stirred at 120 C for 30 min under microwave irradiation using a CEM Discover microwave reactor (the highest power: 85 W; run time: 10 min; hold time: 30 min; temperature: 120 C). The resulting reaction mixture was neutralized with saturated aqueous NaHCO3 solution and extracted with Et2O. The combined organic layers were washed with H2O and dried over Na2SO4, then concentrated under reduced pressure. The crude residue was purified by flash chromatographyon silica gel using hexane/EtOAc as eluent.
With selenium(IV) oxide; In 1,4-dioxane; water; EXAMPLE 1a Preparation of Compound 282 2-Methyl-6-nitroquinoline (0.4 ml, 0.5M solution in dioxane) was treated with selenium dioxide (0 2 ml, 0.9M solution in 9/1 dioxane/water) and heated to 90 C. overnight. The mixture was cooled to room temperature and diluted with water (1 ml). The mixture was then extracted with ethyl acetate (3*2 ml). The organic extract was then dried in vacuo to give 6-nitro-2-quinolinecarboxaldehyde which was carried forward without further purification.

  • 26
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  • [ 90767-09-2 ]
YieldReaction ConditionsOperation in experiment
91% With tetra-(n-butyl)ammonium iodide; ethylene dibromide; urea; In acetonitrile; at 95℃; for 0.833333h;Microwave irradiation; General procedure: 2-Methylquinolines 1(2 mmol), TBAI (2 mmol), urea (2 mmol), 1,2-dibromoethane (6 mL), andacetonitrile (6 mL) were mixed in a microwave tube. The reaction mixture was stirred at 95 C for 30 min under microwave irradiation using a CEM Discover microwave reactor (the highest power: 150 W; run time: 5 min; holdtime: 30 min; temperature: 95 C). The resulting reaction mixture was concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel using hexane/EtOAc as eluent.
81% With tert.-butylhydroperoxide; copper(I) bromide; In water; acetonitrile; at 70℃; for 8h; General procedure: 2-Methylquinoline derivatives (0.5mmol), cuprous halide (0.75mmol), TBHP (8.0 eq., 70% aqueous solution) and CH3CN (2mL) were stirred at 70 C for 8h. Then, the reaction mixture was diluted by water and extracted with CH2Cl2 (3×15mL). The X2 (X=I, Br, Cl) in organic phase was quenched by Na2S2O3. The combined organic layers were washed with saturated NH4Cl aqueous solution and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. The desired product was obtained by silica gel chromatography (petroleum ether/ethyl acetate, v/v=10/1).
63% With N-Bromosuccinimide; In chloroform; at 40℃; for 48h;UV-irradiation; Step A: 2-(bromomethyl)-6-nitroquinoline A solution of <strong>[613-30-9]2-methyl-6-nitroquinoline</strong> (3.0 g, 15.9 mmol) and N-bromosuccinimide (3.11 g, 17.49 mmol) in 36 mL chloroform in a pyrex round bottomed flask was stirred in the presence of a UV lamp at 40 C. for 2 d. After cooling, the mixture was washed with aqueous sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane and the combined organic layers dried over sodium sulfate. Concentration followed by column chromatography on silica gel using hexane:ethyl acetate 7:3 afforded 2-(bromomethyl)-6-nitroquinoline as pale yellow solid (2.67 g, 63%). 1H NMR (300 MHz, DMSO-d6) delta 9.10 (s, 1H), 8.78 (d, J=8.6 Hz, 1H), 8.52 (d, J=9.8 Hz, 1H), 8.23 (d, J=9.2 Hz, 1H), 7.92 (d, J=8.5 Hz, 1H), 4.93 (s, 2H); ES-LCMS m/z 267 (M+H).
  • 27
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  • [ 872537-06-9 ]
  • 28
  • [ 613-30-9 ]
  • 1-ethyl-6-[(6-methoxy-6-oxohexanoyl)amino]-2-methylquinolinium iodide [ No CAS ]
  • 29
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  • 1-ethyl-2-[(1E,3E)-3-(1-ethylquinolin-2(1H)-ylidene)prop-1-enyl]-6-[(6-methoxy-6-oxohexanoyl)amino]quinolinium iodide [ No CAS ]
  • 30
  • [ 613-30-9 ]
  • 6-(5-carboxy-pentanoylamino)-1-ethyl-2-[3-(1-ethyl-1<i>H</i>-quinolin-2-ylidene)-propenyl]-quinolinium; iodide [ No CAS ]
  • 31
  • [ 613-30-9 ]
  • 1-ethyl-2-[3-(1-ethyl-1<i>H</i>-quinolin-2-ylidene)-propenyl]-6-(5-{2-[2-(2-{4-[2-oxo-2-(6-oxo-5,6-dihydro-benzo[<i>e</i>]pyrido[3,2-<i>b</i>][1,4]diazepin-11-yl)-ethyl]-piperazin-1-yl}-ethoxy)-ethoxy]-ethylcarbamoyl}-pentanoylamino)-quinolinium; iodide [ No CAS ]
  • 32
  • [ 613-30-9 ]
  • 3-methyl-12-(3-pyridyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 33
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  • 3-methyl-12-(2-pyridyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 34
  • [ 613-30-9 ]
  • 3-methyl-12-phenyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 35
  • [ 613-30-9 ]
  • 3-methyl-12-(2-methylphenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 36
  • [ 613-30-9 ]
  • 3-methyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 37
  • [ 613-30-9 ]
  • 3-methyl-12-(4-fluorophenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 38
  • [ 613-30-9 ]
  • 3-methyl-12-(4-chlorophenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 39
  • [ 613-30-9 ]
  • 3-methyl-12-[2-(3-methyl)thienyl]-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 40
  • [ 613-30-9 ]
  • 12-cyclohex-3-enyl-3-methyl-8,9,10,12-tetrahydro-7<i>H</i>-benzo[<i>b</i>][4,7]phenanthrolin-11-one [ No CAS ]
  • 41
  • [ 613-30-9 ]
  • 3-methyl-12-(4-methylthiophenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 42
  • [ 613-30-9 ]
  • 12-(4-hydroxyphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 43
  • [ 613-30-9 ]
  • 12-(2,5-dimethoxyphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 44
  • [ 613-30-9 ]
  • 12-(3,4-dihydroxyphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 45
  • [ 613-30-9 ]
  • 12-(3,4-dimethoxyphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 46
  • [ 613-30-9 ]
  • 3-methyl-12-[4-(methoxycarbonyl)phenyl]-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 47
  • [ 613-30-9 ]
  • 12-(2,3-dichlorophenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 48
  • [ 613-30-9 ]
  • 12-(2,4-dimethoxyphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 49
  • [ 613-30-9 ]
  • 3-methyl-12-(4-propoxyphenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 50
  • [ 613-30-9 ]
  • 3-methyl-12-(3,4-methylenedioxyphenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 51
  • [ 613-30-9 ]
  • 12-(2,4-dichlorophenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 52
  • [ 613-30-9 ]
  • 3-methyl-12-[2-(trifluoromethyl)phenyl]-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 53
  • [ 613-30-9 ]
  • 12-(4,4'-biphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 54
  • [ 613-30-9 ]
  • 12-(2,4-dichlorophenyl)-3,9,9-trimethyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 55
  • [ 613-30-9 ]
  • 12-(2,3-dichlorophenyl)-3,9,9-trimethyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 56
  • [ 613-30-9 ]
  • 12-(4-acetoxy-3-methoxyphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 57
  • [ 613-30-9 ]
  • 12-(4-benzyloxyphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 58
  • [ 613-30-9 ]
  • 3-methyl-12-(3,4,5-trimethoxyphenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 59
  • [ 613-30-9 ]
  • 12-(4-benzyloxyphenyl)-3,9,9-trimethyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 60
  • [ 613-30-9 ]
  • 3,9,9-trimethyl-12-(3,4,5-trimethoxyphenyl)-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 61
  • [ 613-30-9 ]
  • 12-(4-benzyloxy-3-methoxyphenyl)-3-methyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-one [ No CAS ]
  • 62
  • [ 613-30-9 ]
  • C26H18N4O6 [ No CAS ]
  • 64
  • [ 613-30-9 ]
  • N-[(S)-3-((R)-2-Methyl-1,2,3,4-tetrahydro-quinolin-6-yl)-2-oxo-oxazolidin-5-ylmethyl]-thioacetamide [ No CAS ]
  • 65
  • [ 613-30-9 ]
  • N-[(S)-3-((R)-2-Methyl-1,2,3,4-tetrahydro-quinolin-6-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide [ No CAS ]
  • 66
  • [ 613-30-9 ]
  • N-({(5S)-3-[(2R)-1-formyl-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide [ No CAS ]
  • 67
  • [ 613-30-9 ]
  • N-[(5S)-3-[(2R)-1-formyl-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide [ No CAS ]
  • 69
  • [ 613-30-9 ]
  • (R)-6-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester [ No CAS ]
  • 73
  • [ 613-30-9 ]
  • (R)-2-Methyl-6-[(R)-5-(4-nitro-benzenesulfonyloxymethyl)-2-oxo-oxazolidin-3-yl]-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester [ No CAS ]
  • 79
  • [ 613-30-9 ]
  • 1-Methoxy-2-methyl-6-nitro-quinolinium; perchlorate [ No CAS ]
  • 80
  • [ 613-30-9 ]
  • [ 117638-85-4 ]
  • 81
  • [ 613-30-9 ]
  • [ 76253-77-5 ]
YieldReaction ConditionsOperation in experiment
98% With tetra-(n-butyl)ammonium iodide; 1,2-dichloro-ethane; urea; at 120℃; for 1h;Microwave irradiation; General procedure: 2-Methylquinolines 1(2 mmol), TBAI (2 mmol), urea (2 mmol), and 1,2-dichloroethane (10 mL) weremixed in a microwave tube. The reaction mixture was stirred at 110 C for 30 min under microwave irradiation using a CEM Discover microwave reactor(the highest power: 150 W; run time: 5 min; hold time: 30 min; temperature:110 C). The resulting reaction mixture was concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel using hexane/EtOAc as eluent.
73% With tert.-butylhydroperoxide; copper(l) chloride; In water; acetonitrile; at 70℃; for 8h; General procedure: 2-Methylquinoline derivatives (0.5mmol), cuprous halide (0.75mmol), TBHP (8.0 eq., 70% aqueous solution) and CH3CN (2mL) were stirred at 70 C for 8h. Then, the reaction mixture was diluted by water and extracted with CH2Cl2 (3×15mL). The X2 (X=I, Br, Cl) in organic phase was quenched by Na2S2O3. The combined organic layers were washed with saturated NH4Cl aqueous solution and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. The desired product was obtained by silica gel chromatography (petroleum ether/ethyl acetate, v/v=10/1).
  • 83
  • [ 613-30-9 ]
  • [ 76253-86-6 ]
  • 84
  • [ 613-30-9 ]
  • [ 76253-91-3 ]
  • 85
  • [ 613-30-9 ]
  • [ 76253-81-1 ]
Same Skeleton Products
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