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[ CAS No. 614-30-2 ] {[proInfo.proName]}

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Chemical Structure| 614-30-2
Chemical Structure| 614-30-2
Structure of 614-30-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 614-30-2 ]

CAS No. :614-30-2 MDL No. :MFCD00035788
Formula : C14H15N Boiling Point : -
Linear Structure Formula :- InChI Key :LXZGVFCKZRHKMU-UHFFFAOYSA-N
M.W : 197.28 Pubchem ID :69191
Synonyms :

Calculated chemistry of [ 614-30-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 3
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 65.14
TPSA : 3.24 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.5
Log Po/w (XLOGP3) : 4.22
Log Po/w (WLOGP) : 3.17
Log Po/w (MLOGP) : 3.61
Log Po/w (SILICOS-IT) : 3.01
Consensus Log Po/w : 3.3

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.12
Solubility : 0.0151 mg/ml ; 0.0000766 mol/l
Class : Moderately soluble
Log S (Ali) : -4.0
Solubility : 0.0198 mg/ml ; 0.0001 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.05
Solubility : 0.00177 mg/ml ; 0.00000899 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.05

Safety of [ 614-30-2 ]

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 [ 614-30-2 ]

* 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 [ 614-30-2 ]

[ 614-30-2 ] Synthesis Path-Downstream   1~29

  • 2
  • [ 100-97-0 ]
  • [ 614-30-2 ]
  • [ 1215-41-4 ]
YieldReaction ConditionsOperation in experiment
With formic acid; ethanol; acetic acid
  • 3
  • [ 64-18-6 ]
  • [ 64-17-5 ]
  • [ 100-97-0 ]
  • [ 614-30-2 ]
  • [ 64-19-7 ]
  • [ 1215-41-4 ]
YieldReaction ConditionsOperation in experiment
anschliessendes Behandeln mit wss.Salzsaeure;
  • 4
  • [ 614-30-2 ]
  • [ 1215-41-4 ]
YieldReaction ConditionsOperation in experiment
With formaldehyd; 4-hydroxyl-amino-toluene-sulfonic acid-(2) man zersetzt das Reaktionsprodukt durch Kochen mit verd. Natronlauge;
  • 5
  • [ 100-44-7 ]
  • [ 100-61-8 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine; In methanol; at 20℃; for 12.0h; A solution of N-methylaniline (814 muL, 7.5 mmol), benzyl chloride (574 muL, 5.0 mmol), and triethylamine (697 muL, 5.0 mmol) in methanol (5 mL) was stirred for 12 h at room temperature. The resulting mixture was diluted with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. Purification of the residue by chromatography on silica gel (hexane/ethyl acetate = 10/1 to 5/1 as the eluent) afforded 1g (842 mg, 85% yield) as a yellow oil.
  • 6
  • [ 614-30-2 ]
  • [ 14683-47-7 ]
YieldReaction ConditionsOperation in experiment
66% With n-butyllithium; potassium <i>tert</i>-butylate In hexane for 48h; Heating;
  • 7
  • [ 614-30-2 ]
  • [ 874-46-4 ]
  • Benzyl-methyl-[4-([1,2,4]triazolo[1,5-a]pyridin-2-ylazo)-phenyl]-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sulfuric acid; sodium nitrite 1.) H20, glacial acetic acid, 0 deg C - 5 deg C, 2.) H2O, glacial acetic acid, below 5 deg C; Multistep reaction;
  • 8
  • [ 108-90-7 ]
  • [ 103-67-3 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
94% With C33H40ClN3O2Pd; potassium tert-butylate; In toluene; at 90℃; for 6.0h;Inert atmosphere; Schlenk technique; Sealed tube; General procedure: Under a N2 atmosphere, KOtBu (102.1 mg, 1.3 equiv) and a so-lution of complex 3a (10e50 mL, 0.01e0.05 mol%, prepared from4.6 mg of complex 3a in 1.0 mL dichloromethane) were added into aSchlenk reaction tube. The tube was sealed and the solvent wasremoved under reduced pressure. Then toluene (0.5 mL), amines(0.84 mmol) and aryl chlorides (0.70 mmol) were successivelyadded. The mixture was stirred vigorously at the specied tem-perature for 3e24 h. Then the solvent was removed under reducedpressure and the residue was puried by ash column chroma-tography (SiO2) to give the corresponding products.
88% With PdCl2(C3H3N2(CH3))(C3H2N2(C6H3(C3H7)2)2); potassium tert-butylate; In 1,4-dioxane; at 70℃; for 3.0h;Inert atmosphere; General procedure: Under N2 atmosphere, KOtBu (1.0 mmol), NHC-Pd(II)-Im 2a (1.0 mol %), dry dioxane (1.0 mL), morpholine 3 (0.8 mmol), and aryl chloride 4 (0.7 mmol) were successively added into a Schlenk reaction tube. The mixture was stirred at 70 C for 3 h. The solvent was removed under reduced pressure and the residue was purified by a flash chromatograph on silica gel to give the pure products 5.
86% With C40H44ClN3Pd; potassium tert-butylate; In toluene; at 110℃; for 24.0h;Inert atmosphere; General procedure: Under N2 atmosphere, KOtBu (1.3 equiv), toluene (1.0 mL), amines 5 (0.84 mmol), aryl chlorides 4 (0.7 mmol) and finally a solution of complex 3a (20-100muL, 0.01-0.05 mol%, prepared from 0.014 mmol 3a in 4.0mL toluene) were successively added into a Schlenk reaction tube. The mixture was stirred vigorously at 110 C for 24h. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding products.
84% With tris-(dibenzylideneacetone)dipalladium(0); di(dicyclohexylamino)phenylphosphine; potassium tert-butylate; In toluene; for 4.0h;Reflux; Inert atmosphere; General procedure: A dried resealable Schlenk tube was charged with Pd2(dba)3 (0.03 mmol, 1 mol % of Pd), amine (3.0 mmol), ligand 1 (1 mol %) and KOtBu (4.5 mmol) in dried toluene (20 mL). The Schlenk tube was capped with a rubber septum, evacuated, and backfilled with nitrogen. This evacuation/backfill sequence was repeated two or three additional times. Aryl chloride (3.15 mmol) and toluene (2 mL×2) were added through the septum. After the septum was replaced with a Teflon screwcap, the mixture was refluxed until the starting amine had been completely consumed as judged by GC or TLC. The reaction mixture was then cooled to room temperature, diluted with dichloromethane (10 mL×2), filtered, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel using n-hexane/dichloromethane (1/1, v/v) to afford C-N coupled product.

  • 9
  • [ 614-30-2 ]
  • [ 71-43-2 ]
  • [ 1215-41-4 ]
YieldReaction ConditionsOperation in experiment
at 20℃;
  • 10
  • [ 1934-92-5 ]
  • [ 614-30-2 ]
  • [ 6941-23-7 ]
YieldReaction ConditionsOperation in experiment
1: 77% 2: 8% With titanocene difluoride; methylphenylsilane In toluene at 80℃;
1: 77% 2: 8% With titanocene difluoride; methylphenylsilane In toluene at 80℃; for 1h;
  • 11
  • [ 591-50-4 ]
  • [ 103-67-3 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; copper(l) iodide; ethylene glycol; In isopropyl alcohol; at 20℃;Inert atmosphere; General procedure: A mixture of CuI (10 mmol%) and K3PO4 (3.0 equiv.) was taken in a two necked round bottom flask evacuated and backfilled with nitrogen and fitted on oil bath. 2-Propanol (10 mL), ethylene glycol (1.1 mL), 1,2,3,4-tetrahydroisoqunoline (15 mmol, 2.0mL) and aryl iodide (10 mmol, 1.12 mL) were added successively by microsyring at rt. The reaction mixture was heated at 80-90 oC with stirring for 24-36 h. After the completion of the reaction was allowed to cool at rt. Diethyl ether (20 mL) and water (20 mL) was added to reaction mixture. The organic layer was extracted by diethyl ether (2 × 20mL). The combined organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by rotary evaporator and the crude product was purified by column chromatography on silica gel with a mixture of hexane/ethyl acetate as eluent to afford an analytically pure sample of substrates 1.
  • 12
  • [ 108-86-1 ]
  • [ 103-67-3 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
93.24% With C31H38N5P; caesium carbonate; bis(dibenzylideneacetone)-palladium(0); In tert-Amyl alcohol; at 100℃;Inert atmosphere; To a 25 mL reaction tube with a branch tube was added 0.25 g (1.592 mmol) bromobenzene, 0.20 g (1.866 mmol) N-methylaniline, 0.78 g (2.394 mmol) cesium carbonate, and 2.5 mL tert-amyl alcohol. The air in the reaction system was replaced 3 times with nitrogen. Under nitrogen protection, 9 mg (0.016 mmol) of Pd(dba) 2, 17 mg (0.032 mmol, 97%) of L2 ligand were added. The air in the reaction system was replaced 3 times with nitrogen. Slowly warm up to 100C, and react for 0.5-1 hour under the protection of nitrogen. After the reaction was completed, it was cooled to room temperature, 15 mL of water was added, extracted three times with ethyl acetate (3×15 mL), and washed once with 30 mL of saturated brine. After drying with 5 g of anhydrous sodium sulfate, it was desolvated (55 C., 50 mbar). The product N-methyldiphenylamine was then obtained by column chromatography using ethyl acetate and petroleum ether. The liquid detection purity was 98.5%, the raw material conversion rate was 100%, and the yield was 95.10%.
  • 13
  • [ 100-61-8 ]
  • [ 100-51-6 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
91% at 160℃; for 28.0h;Inert atmosphere; N-methylaniline (217 mg, 2 mmol), benzyl alcohol (1101 mg, 10 mmol) and 40 mg 2.28% Pd/Fe2O3 were added into a 50 mL reaction tube and reacted under Argon atmosphere at 160 oC for 28 h. The crude mixture was purified by column chromatograph (ethyl acetate / triethylamine / petroleum ether = 1/1/200, v/v/v; Silica Gel: 200-300 mesh; Rf = 0.29). Following the procedure above, N-benzyl-N-methylaniline was obtained as a light yellow liquid (364 mg, Isolated yield = 91%). 1H NMR (400MHz, CDCl3, ppm): delta 7.20-7.33 (m, 7H), delta 6.71-6.76 (m, 3H), delta 4.53 (s, 2H), delta 3.01 (s, 3H); 13C NMR (100MHz, CDCl3, ppm): delta 149.74, 139.02, 129.14, 128.52, 126.82, 126.71, 116.52, 112.35, 56.61, 38.47. m/z (rel. int.) 198(16), 197(98), 196(31), 180(6), 121(7), 120(75), 118(7), 106(8), 105(7), 104(12), 92(11), 91(100), 78(5), 77(26), 65(17), 51(9), 39(6).
70%Chromat. With CuO#NiO; at 110℃; for 18.0h;Inert atmosphere; [0044] With reference to the conditions used in Examples 9-16, 60-150 mg of catalyst D obtained in Example 4 was weighted and added into a 40 mL glass reaction tube provided with a magnetic stirring apparatus containing 5 mmol amines having different structures and 5 mmol alcohols having different structures, respectively. After sealed, the tube was purged with N2 to replace the air in the system for three times. Next, the system was heated and stirred. The temperature was raised to 80-180 C. and then kept for 6-36 hours. The reaction was then stopped and the system was cooled down to the room temperature. The catalyst was obtained from the reaction mixture by filtration. Agilent 7890A (30 m×0.25 mm×0.33 mum capillary column, hydrogen flame ionization detector) gas chromatograph was used for quantitatively analyzing the reaction mixture. The other byproducts were qualitatively analyzed with Agilent 6890/5973 Gas Chromatography-Mass Spectrometer (equipped with NIST Mass Spectral Database chemical workstation, 30 m×0.25 mm×0.33 mum capillary column). Each of the analysis results was shown in Table 2.
  • 14
  • [ 140-11-4 ]
  • [ 100-61-8 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
82% With 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine In ethanol at 80℃; for 72h;
  • 15
  • [ 1934-92-5 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
93% With bis(trimethylsilyl)amide yttrium(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In toluene; at 100℃; for 24.0h;Inert atmosphere; Under nitrogen protection, add the raw materials N-benzyl-N-methylbenzamide (0.5 mmol), pinacol borane (1.2 mmol) and catalyst Y[N(SiMe3)2]3 (10 mol%), In toluene (3 ml), the reaction was carried out at 100 C for 24 h, and the product separation yield was 93%.
64% With sodium triethylborohydride; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 80℃; for 6.0h;Inert atmosphere; Sealed tube; Under an argon atmosphere, the amide substrate (0.5 mmol), borane (1.5 mmol, 3.0 equiv.), THF (2 mL), and sodium triethylborohydride (4 mol%) were added to a 10 mL sealed tube in this order, and The reaction mixture was placed in an oil bath at 80 C. and stirred for 6 hours. After the reaction was completed, the reaction was quenched by exposure to air, and then the product was separated directly by column chromatography. The yield was 64%. NMR data of the product:
  • 16
  • [ 614-30-2 ]
  • [ 22979-35-7 ]
  • [ 1262227-15-5 ]
YieldReaction ConditionsOperation in experiment
85% With copper acetylacetonate; In dichloromethane; at 20℃; for 6.0h;Inert atmosphere; A 0.003 M dichloromethane solution of copper(II) acetylacetonate (1.0 mL, 0.003 mmol) [prepared from copper(II) acetylacetonate (12 mg, 0.046 mmol) and dichloromethane (15 mL)], and a 0.015 M dichloromethane solution of trifluoromethanesulfonic acid (0.20 mL, 0.003 mmol) [prepared from trifluoromethanesulfonic acid (15 muL, 0.17 mmol) and dichloromethane (11 mL)] was added to a flask containing 1g (89 mg, 0.45 mmol) with stirring at room temperature under an argon atmosphere. Then, a solution of diazoester 2a (53 mg, 0.30 mmol) in dichloromethane (1.8 mL) was added dropwise to the flask. After stirring for 6 h at the same temperature, the resulting mixture was quenched with saturated sodium hydrogen carbonate and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. Purification of the residue by chromatography on silica gel (hexane/ethyl acetate = 5/1 as the eluent) afforded 3ga (88 mg, 85% yield) as a pale pink oil.
  • 17
  • [ 614-30-2 ]
  • [ 93961-29-6 ]
  • [ 1262227-20-2 ]
YieldReaction ConditionsOperation in experiment
90% With copper acetylacetonate; boron trifluoride diethyl etherate; In dichloromethane; at 20℃; for 6.0h;Inert atmosphere; General procedure: A 0.003 M dichloromethane solution of copper(II) acetylacetonate (1.0 mL, 0.003 mmol) [prepared from copper(II) acetylacetonate (12 mg, 0.045 mmol) and dichloromethane (15 mL)], and a 0.006 M dichloromethane solution of boron trifluoride diethyl etherate (0.50 mL, 0.003 mmol) [prepared from boron trifluoride diethyl etherate (15 muL, 0.12 mmol) and dichloromethane (20 mL)] was added to a flask containing 1a (87 mg, 0.45 mmol) with stirring at room temperature under an argon atmosphere. Then, a solution of diazoester 2a (53 mg, 0.30 mmol) in dichloromethane (1.5 mL) was added dropwise to the flask. After stirring for 6 h at the same temperature, the resulting mixture was quenched with saturated sodium hydrogen carbonate and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. Purification of the residue by chromatography on silica gel (hexane/ethyl acetate = 5/1 as the eluent) afforded 3a (91 mg, 89% yield) as a pale pink oil.
  • 18
  • [ 100-61-8 ]
  • [ 87100-28-5 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
99% With di-tert-butyl peroxide; copper diacetate In toluene at 50℃; for 24h; Sealed tube; Inert atmosphere;
  • 19
  • [ 758640-21-0 ]
  • [ 124-38-9 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
> 95% With diphenylsilane; caesium carbonate; In acetonitrile; at 80℃; under 750.075 Torr; for 72.0h;Schlenk technique; Inert atmosphere; 1) In a glove box, 0.25 mmol of N-benzylaniline,6 equiv (1.5 mmol) of diphenylsilane,10 mol% (based on N-benzylaniline) of cesium carbonate,1.6 ml of acetonitrile solvent was added to 50 ml of a Schlenk tube protected with N2. 2) The N2 in the Schlenk tube was replaced by CO2 in the double-row tube under refrigeration vacuum operation,The pressure of CO2 is 1 bar. 3) using said cesium carbonate as a catalyst,Said carbon dioxide being a C1 source,The diphenylsilane is used as a reducing agent,The 4-fluoro-N-methylaniline was reacted in an acetonitrile solvent at 80 C for 72 hours. 4) After completion of the reaction,To the Schlenk tube was added 0.2 mmol of ferrocene as the internal magnetic standard. 5) By Bruker NMR analysis,The resulting NMR spectrum of the product is consistent with the corresponding pure mass spectrum reported in the literature (M.-C. Fu, R. Zhang, W.-M. Cheng, Y. Fu, Angewandte Chemie International Edition 2015, 54, 9042-9046.N-methyl-N-benzylaniline in this exampleYield> 95%.
  • 20
  • [ 614-30-2 ]
  • [ 36271-19-9 ]
YieldReaction ConditionsOperation in experiment
92% With rhodium(III) chloride hydrate; dihydrogen peroxide; In water; at 50℃; for 4.0h; General procedure: A 25 mL round bottomed flask equipped with a magnetic stirrerbar was charged with tertiary amine (1 mmol), 1 (1.2 mmol), RuCl3nH2O (5 mol %, 0.05 mmol) and the resulting reaction mixture was stirred at 50 C. The aqueous hydrogen peroxide(2.5 mmol, 35 wt %) was added drop wise to the stirred mixture and the progress of the reaction was monitored by TLC (SiO2). After completion of the reaction, the product was extracted from the PEG layer with diethyl ether. The combined organic layer was dried over anhydrous sodium sulfate followed by the usual work-up to yield corresponding a-aminonitrile. The conversion of the tertiary amine and selectivity for the desired product was determined by GC-MS and the identity of the products was established by comparing their spectral data with authentic samples.
  • 21
  • [ 64-18-6 ]
  • [ 758640-21-0 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
88% With dipotassium hydrogenphosphate; 18-crown-6 ether; In tetrahydrofuran; at 80℃; for 12.0h;Molecular sieve; General procedure: In air, K2HPO4 (10 mol %, 4.35mg), PMHS (242 mul), amine (0.25 mmol), formic acid (4.6equiv ,43.3mul), 18-crown-6 (20mol %, 13.2mg) 4A MS(10mg) and 2 ml THF were added into a tube equipped with a water condenser. The reaction mixturewas stirred at 80C for 12 hours. The yields of isolated products were reported. The mixture was filtered through a silica gelcolumn with petroleum ether and ethyl acetate as the eluent. The resultant solution was concentrated and purified by silica gelcolumn chromatography to give the corresponding product.
  • 22
  • [ 64-18-6 ]
  • [ 538-51-2 ]
  • [ 614-30-2 ]
YieldReaction ConditionsOperation in experiment
93% With platinum on activated charcoal; phenylsilane; In toluene; at 80℃; for 15.0h;Schlenk technique; Inert atmosphere; A,An activated carbon supported platinum catalyst (Pt / C, 0.18 mg platinum, 0.0009 mmol, 0.3 mol%) was added to a 10 mL Schlenk tube,After evacuation of argon, add solvent (toluene) 1mL;The activated carbon supported platinum catalyst is used in an amount of 0.3% of the amount of the starting material V-1,The ratio of the amount of the starting material V-1 to the number of milliliters of the solvent toluene is 0.3;B,Under argon protection,To the above system,Separately, phenylsilane (94.7 mg, 0.9 mmol) was added successively,(R4 = phenyl, R5 = phenyl) (54.4 mg, 0.3 mmol) and formic acid (27.6 mg, 0.6 mmol);The ratio of the amount of the benzene silane to the starting material V-1 is 3.0;The ratio of the amount of the formic acid to the starting material V-1 substance is 2.0;C,The whole reaction system was stirred at 80 C to carry out the reaction;The reaction time was 15 hours;D,After completion of the reaction, 3 mL of ethyl acetate was added to the system,The reaction was quenched with aqueous sodium hydroxide (3 mol / L, 3 mL)Ethyl acetate (3 x 10 mL), the organic phase was separated,Dried over anhydrous Na2SO4, filtered, and evaporated to remove the solvent by evaporation.The residue was purified by ethyl acetate / petroleum ether mixed solvent column chromatography,Separation and purification gave the target product VI-155.0 mg in 93% yield.The ratio of the ethyl acetate / petroleum ether mixed solvent is 1: 100,Column chromatography using silica gel as the stationary phase.
  • 23
  • [ 614-30-2 ]
  • [ 57957-24-1 ]
  • N-(1-benzyl-4-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With tert.-butylhydroperoxide; iron(III) chloride In nonane; acetonitrile at 60℃;
23% With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) In dimethyl sulfoxide at 50℃; for 12h; General procedure for oxidative Povarov reaction using Fe(phen)3(PF6)3 under air: General procedure: To a solution of dimethylaniline 1 (1.0 mmol, 5 equiv.) in dimethyl sulfoxide (2 mL), enamide 2 (0.2mmol) and Fe(phen)3(PF6)3 (14.4 mg, 14 μmol, 7 mol %) were added at room temperature. The reaction mixture was heated at 50 °C, and stirred for 12 h under air. After cooling to room temperature, the organic layer was extracted with ethyl acetate and water, and the combined organic solution was dried under magnesium sulfate and filtered. The resulting solution was concentrated and purified by silica gel column chromatography to provide the tetrahydroquinoline product 3.
  • 24
  • [ 941-69-5 ]
  • [ 614-30-2 ]
  • (3aR*,9bS*)-5-benzyl-2-phenyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tert.-butylhydroperoxide; tris(1,10-phenanthroline)iron(II) bishexafluorophosphate In decane; acetonitrile at 20℃; for 12h; Inert atmosphere;
46% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; 1,2-dichloro-ethane at 70℃; for 12h; 22 General procedure for product synthesis: General procedure: To a screw cap reaction vial, maleimide (0.1 mmol, 1 equiv), tertiary aniline[1] (0.2 mmol, 2 equiv), tetrabutyl ammonium iodide 3.69 mg (TBAI, 10 mol%), TBHP 55 µL (70% in H2O, 0.4 mmol, 4 equiv) and DCE (1.0 mL) were added. The reaction mixture was heated to 70 °C. The reaction progress was monitored by thin layer chromatography (ethyl acetate/petroleum ether mixture) and GC-MS. Upon completion, the crude reaction mixture was concentrated under reduced pressure and subsequently purified by flash column chromatography over silica gel using petroleum ether/ethyl acetate as eluent system.
42% With 1,4-diphenyl-but-2-ene-1,4-dione In 1,4-dioxane Irradiation;
12% With tert.-butylhydroperoxide; cobalt(II) chloride In decane; acetonitrile at 60℃; for 5h; Inert atmosphere; Sealed tube; General procedure for the cobalt-catalyzed oxidative annulation of aromatic tertiary amines with N-substituted maleimides General procedure: To a screw-capped tube (5 mL) containing freshly distilled MeCN (2.0-3.0 mL) was successively added CoCl2 (0.10 equiv for N-substituted maleimide), an aromatic tertiary amine (2.0 equiv for N-substituted maleimide), an N-substituted maleimide (0.50-1.0 mmol), and 5.5 M TBHP in decane solution (1.5 equiv for N-substituted maleimide) under N2 atmosphere. After the tube was sealed with a cap that contained a PTFE septum, the resultant mixture was stirred at 60 °C (bath temperature). After cooling to room temperature, the mixture was passed through a silica gel-packed short column (EtOAc as the eluent), and the filtrate was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane : EtOAc =5 : 1) to give the corresponding tetrahydroquinoline derivative. If necessary, the isolated product was further purified by a preparative HPLC equipped with a GPC column (chloroform as the eluent).

  • 25
  • [ 1555-66-4 ]
  • [ 827-94-1 ]
  • [ 614-30-2 ]
  • C18H14Br2N6O2 [ No CAS ]
  • C20H16Br2N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,6-dibromo-4-nitroaniline With sulfuric acid at 25 - 35℃; for 2h; Stage #2: With nitrosylsulfuric acid at 20 - 28℃; Stage #3: N,N-bis(2-cyanoethyl)aniline; N-methyl-N-phenyl-benzenemethanamine With sulfuric acid; aminosulfonic acid In water at 0 - 70℃; for 5h; Overall yield = 94.4 %; 2 Example 2 14.8 g of 2,6-dibromo-4-nitroaniline was added to 12 g of 98% sulfuric acid at 25 to 35 ° C and stirred2 hours.Maintaining at 20 ~ 28 slowly dropping 16.4 g of 40% nitrosyl sulfuric acid solution, and then continue to protectHolding at this temperature for 2 to 4 hours to complete the diazotization reaction.2 g of N, N -dicyanoethylaniline, 8.2Methyl-N-benzylaniline, 90 mL of water, 10 mL of sulfuric acid and 0.2 mL of sulfamic acid to prepare a mixed solutionLiquid, and the prepared diazo solution in the 0-8 ° C coupling reaction, the reaction temperature increased to 3 hours after the65-70 ° C for 2 hours, filtration, washing the product to eluate pH value of 6-7, in compound 3 and4, the yield of the mixed filter cake was 94.4%. The total content of the combined product was 94.3% by HPLC analysis.
  • 26
  • [ 614-30-2 ]
  • [ 33513-42-7 ]
  • [ 1215-41-4 ]
YieldReaction ConditionsOperation in experiment
91% With trichlorophosphate
  • 27
  • [ 614-30-2 ]
  • [ 4873-09-0 ]
  • C17H20N(1+)*C7H7O3S(1-) [ No CAS ]
  • 28
  • [ 614-30-2 ]
  • [ 90719-30-5 ]
  • C18H19NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 24℃; for 24h; Irradiation; Inert atmosphere; stereoselective reaction;
  • 29
  • [ 614-30-2 ]
  • [ 13380-67-1 ]
  • 5-benzyl-2-(4-bromophenyl)-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With eosin Y disodium salt; In 1,4-dioxane; at 20℃; for 24h;Irradiation; General procedure: In an 8.0 mL glass vial quipped with stir bar was addedunsymmetric tertiary amine (1.2 mmol), dioxane (1.5 mL), maleimide (0.3 mmol), Eosin Y (0.015 mmol) and the solution wasirradiated under four 10 W blue LEDs for 24 h in ambient tem-perature. The reaction was stopped and solvent was removed undervacuum. The residue was dissolved in ethyl acetate and washedwith water. Again, solvent was removed under vacuum. The crudeproduct was puried by column chromatography using 60e200silica gel (Eluent; Ethyl acetate:Hexane 15:85).
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