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[ CAS No. 15485-32-2 ] {[proInfo.proName]}

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Chemical Structure| 15485-32-2
Chemical Structure| 15485-32-2
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Product Details of [ 15485-32-2 ]

CAS No. :15485-32-2 MDL No. :MFCD00018781
Formula : C14H12ClN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 229.71 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 15485-32-2 ]

* 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 [ 15485-32-2 ]

[ 15485-32-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 104-88-1 ]
  • [ 106-49-0 ]
  • [ 15485-32-2 ]
YieldReaction ConditionsOperation in experiment
100% for 6h; Ambient temperature;
96% In ethyl 2-hydroxypropionate at 20℃; for 0.0333333h;
96% With montmorillonite at 20℃; for 0.1h; Neat (no solvent);
95%
92% In ethanol Heating;
88% With acetic acid In ethanol for 3h; Reflux; 2. 2. Procedure for the Preparation of Schiff Bases 1a-10a General procedure: To a 100 mL round bottomed flask containing 25 mL absolute ethanol, aromatic aldehyde (4.5 mmol) and 3 drops of glacial acetic acid, equipped with condenser and stirring bar, aromatic amine (4.5 mmol) dissolved in absolute ethanol (10 mL) was added. The reaction mixture was refluxed for 3 h, then cooled down to room temperature. Product was collected as a solid by filtration and recrystallized from ethanol.
83% With magnesium sulfate; acetic acid In dichloromethane at 20℃; for 18h; Inert atmosphere; N-(4-Chlorobenzylidene)-4-methylaniline (5a) To a soln of 4-chlorobenzaldehyde (5.62 g, 40.0 mmol) and p-toluidine (4.29 g, 40.0 mmol) in CH2Cl2 (30 mL) were added AcOH (0.3 mL) and MgSO4 (6 g). After stirring for 18 h at 20 °C, the suspensionwas filtered. The filtrate was washed with sat. aq NaHCO3 (10 mL) and dried (Na2SO4), and the solvent was removed in vacuoto give pink-colored crystals; yield: 7.61 g (83%); mp 126.1-126.7 °C; Rf = 0.21 (cyclohexane-EtOAc, 15:1).
79% With acetic acid In methanol Reflux;
75% With chitosan In ethanol; water at 20℃; for 3.16667h;
In ethanol for 2h; Heating;
at 20℃; for 1h;
In methanol at 20℃; for 1h;
for 2h; Reflux;
With acetic acid at 20℃; for 4h;
Reflux;
In ethanol for 3h; Reflux;
In methanol at 20℃;
In ethanol for 0.5h; Reflux;
With 1-butyl-1-methylpyrrolidinium hydrogen sulfate In ethanol at 20℃;
In acetonitrile at 20℃; for 24h; Molecular sieve; Inert atmosphere; Preparation of imines and related compounds General procedure: Equimolar amounts of the corresponding aldehyde and amine (1:1, 2 mmol) together with 2 g of activated MS 4 Å were placed in a 50 mL flask, 10 mL of dry ACN were added and the solution was stirred under nitrogen for 24 h or until all the starting material was consumed. The reaction progress was monitored by TLC or HPLC. After the reaction was complete, 10 mL of saturated aqueous NaHCO3 solution were added. Molecular sieves were filtered and washed with 20 mL of EtOAc. The aqueous layer was extracted with 3 × 10 mL of EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude imine was used without further purification.
In ethanol Heating;
at 20℃; for 1h; Milling;
With acetic acid In dichloromethane at 20℃;
In ethanol Reflux;
at 20℃; for 0.833333h; Milling; Sealed tube;
With calcium sulfate In toluene Reflux; 4.2 General procedure for the preparation of imines (5) Distilled benzaldehyde (50 mmol, 5.1 ml) in toluene (8 ml) was added to a solution of distilled aniline (50 mmol, 4.56 ml) in dry toluene (50 ml). The mixture was heated under reflux for 7 h in the presence of CaSO4. The mixture was filtered and then the solvent was evaporated. The crude products were obtained as solid and recrystallized from hexane.
With alizarin red S-sensitized TiO2 In acetonitrile for 0.5h; 2.3 Procedure for the photocatalytic oxidative synthesis of imines from alcohols and amines General procedure: 107.6mgARS-sensitized TiO2 (consisting of 106.7mg TiO2 and 2.66×10-3 mmol ARS) was dispersed with the ultrasonic instrument in a 20mL Pyrex vessel with 10mL anhydrous CH3CN for 5min. Then 0.4mmol alcohol 1 and 10μL chlorobenzene (the internal standard) were added to the reaction for another 5min ultrasonication. The BET specific surface areas of TiO2 and ARS-TiO2 are 275m2/g and 237m2/g respectively and the XRD characterizations are in Figure S1. The reaction mixture stirred 30min in dark for the adsorption equilibrium. Subsequently, O2 was injected into the sealed vessel to reach 0.1MPa. The reaction mixture was magnetically stirred at 1500rpm and simultaneously illuminated with 3W green LEDs for 2h (alcohols 1c, 1d, 1e for 2.5h) at room temperature for the total transformation from alcohols to aldehydes. Before the further condensation, the reaction mixture should be moved away from irradiation of green LEDs, and the reaction pressure should be released. Then 1.0 equivalent of amine 2 was introduced into the mixture. The transformation was magnetically stirred at 400rpm for 30min at room temperature. The ARS-sensitized TiO2 nanoparticles were separated from the reaction mixture by centrifugation (10,000rpm, 7min) and the liquid phase was purified by syringe filter (25mm, 0.45μm, PTFE). The photocatalyst nanoparticles were dispersed in 25mL CH3CN and repeated the processes of centrifugation and purification. The organic phase was combined, followed by rotary evaporation for 30min at room temperature. Finally, the desired imine 3 was obtained. The isolated imines were confirmed by 1H NMR and 13C NMR spectra and HRMS.
Multi-step reaction with 2 steps 1: palladium on activated charcoal; ammonium formate / isopropyl alcohol; water / 1 h / 20 °C 2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; oxygen / acetonitrile / 35 °C / Molecular sieve; Irradiation
With indium(III) chloride In toluene for 1h; Reflux; General Procedure for the Preparation of 4a-f General procedure: An equimolar mixture of aromatic amines 1 (1.0 mmol) andaromatic aldehydes 2 (1.0 mmol) in presence of 10 mol% of InCl3 were refluxed in 5 mL of toluene. Then after refluxing for 1 h (as indicated by TLC), 2-ethynylaniline 3 (1.0 mmol) was added to reaction pot and refluxed the system for another 23 h. Then, the completions of the reactions were monitoredby UV-lamp (giving distinct blue/green colouration). The reaction mixture was brought to room temperature and extracted with ethylacetate (2 × 10 mL). The organic layer containingthe quinoline was dried over anhydrous Na2SO4 and then evaporated. The crude residue was purified by column chromatography over silica gel using ethyl acetate/petroleum ether(1:5) as eluent to afford pure product 4a-i in good yields.

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  • 3
  • [ 15485-32-2 ]
  • [ 4294-57-9 ]
  • [ 613-33-2 ]
  • [ 1254576-63-0 ]
  • 4
  • [ 51411-04-2 ]
  • [ 15485-32-2 ]
  • 2-(2-(4-chlorophenyl)-4-oxo-1-(p-tolyl)azetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
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