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Chemical Structure| 142729-99-5 Chemical Structure| 142729-99-5

Structure of 142729-99-5

Chemical Structure| 142729-99-5

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Product Details of [ 142729-99-5 ]

CAS No. :142729-99-5
Formula : C13H13NO2
M.W : 215.25
SMILES Code : O=C(C1=NC2=CC=CC=C2C(C)=C1)OCC

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Application In Synthesis of [ 142729-99-5 ]

* 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 [ 142729-99-5 ]

[ 142729-99-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 5256-74-6 ]
  • [ 52562-19-3 ]
  • [ 142729-99-5 ]
YieldReaction ConditionsOperation in experiment
76% With rhodium(II) acetate; copper diacetate; sodium carbonate; In 1,2-dichloro-ethane; at 100℃; for 24h;Schlenk technique; In a 25 mL Schlenk reaction tube equipped with a magnetic stirrer,<strong>[52562-19-3]2-isopropenylaniline</strong> (0.2 mmol, 1.0 eq.) Was added,Rhodium acetate (0.01 mmol, 5 mol%),Copper acetate (0.4 mmol, 2.0 eq.),Sodium carbonate (0.4 mmol, 2.0 eq.),1,2-dichloroethane (2 mL) and diethyl diazo malonate (0.4 mmol, 2.0 eq.).The reaction tube was placed in a heating module at 100 C,Reaction 24h, TLC detection to complete reaction.The reaction solution was cooled to room temperature,After adding 10 mL of ethyl acetate, the catalyst was removed by filtration through a short column of silica gel,Transferred to a 50 mL round bottom flask,Add a small amount of silica gel, spin dry,The crude product was purified by flash column chromatography,To give ethyl 4-methylquinoline-2-carboxylate (Formula a) in 76% yield.
76% With dirhodium tetraacetate; copper diacetate; sodium carbonate; In 1,2-dichloro-ethane; at 100℃; for 16h;Sealed tube;Catalytic behavior; General procedure: To a 25mL tube containing a magnetic stir bar, was added 2-vinylanilines 1 (0.2mmol), Rh2(OAc)4 (0.01mmol, 5mol%), Cu(OAc)2 (0.4mmol, 2.0 equiv), Na2CO3 (0.4mmol, 2.0 equiv), 1,2-DCE (2mL), and α-diazocarbonyl compounds 2 (0.4mmol, 2 equiv). The resulting mixture was stirred at 100C in air in sealed tube for 16h. After being cooled to room temperature, the reaction was monitored by TLC and the solvent was evaporated under reduced pressure. Purification was carried out by column chromatography using a mixture of ethyl acetate and petroleum ether (1:10 to 1:20) as eluent to obtain the desired product 3.
  • 2
  • [ 28383-65-5 ]
  • [ 52562-19-3 ]
  • [ 142729-99-5 ]
YieldReaction ConditionsOperation in experiment
45% With dirhodium tetraacetate; copper diacetate; sodium carbonate; In 1,2-dichloro-ethane; at 100℃; for 16h;Sealed tube; General procedure: To a 25mL tube containing a magnetic stir bar, was added 2-vinylanilines 1 (0.2mmol), Rh2(OAc)4 (0.01mmol, 5mol%), Cu(OAc)2 (0.4mmol, 2.0 equiv), Na2CO3 (0.4mmol, 2.0 equiv), 1,2-DCE (2mL), and α-diazocarbonyl compounds 2 (0.4mmol, 2 equiv). The resulting mixture was stirred at 100C in air in sealed tube for 16h. After being cooled to room temperature, the reaction was monitored by TLC and the solvent was evaporated under reduced pressure. Purification was carried out by column chromatography using a mixture of ethyl acetate and petroleum ether (1:10 to 1:20) as eluent to obtain the desired product 3.
 

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