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Chemical Structure| 124797-01-9 Chemical Structure| 124797-01-9

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Chemical Structure| 124797-01-9

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Product Details of [ 124797-01-9 ]

CAS No. :124797-01-9
Formula : C9H10ClNO2
M.W : 199.63
SMILES Code : O=C(OCC)C1=C(CCl)N=CC=C1
MDL No. :MFCD10697612

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Application In Synthesis of [ 124797-01-9 ]

* 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 [ 124797-01-9 ]

[ 124797-01-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1721-26-2 ]
  • ethyl acetate n-hexane [ No CAS ]
  • [ 937-14-4 ]
  • [ 124797-01-9 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate; In dichloromethane; 1,2-dichloro-ethane; EXAMPLE 2 Preparation of ethyl 2-chloromethylnicotinate A solution of 9 g of <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> in 250 mL methylene chloride is stirred at room temperature and 32 g of 80percent metachloroperoxybenzoic acid is added in one portion. The resulting solution is stirred for three days. The precipitated solid is filtered off, and the filtrate is washed with cold, dilute aqueous sodium hydroxide, dried, and concentrated in vacuo to afford the crude N-oxide. This material is digested in 75 mL of 1,2-dichloroethane; 15 mL of phosphorous oxychloride is added, and the solution is heated at reflux overnight. The solution is concentrated in vacuo, and the residue is taken up in methylene chloride and neutralized with aqueous sodium acetate. The organic phase is dried, concentrated in vacuo, and the residue is chromatographed on silica gel using hexane-ethyl acetate mixtures to afford 1.2 g of the title product as an oil having NMRdeltamCDCl(3): 1.4 (+, 3H), 4.5 (q, 2H), 5.1 (2H), 7.4 (1,H), 8.4 (dd, 1H), 8.8 (dd, 1H). Also prepared by this method is ethyl 2-chloromethylquinoline-3-carboxylate; NMR(deltaCDCl3) 1.4 (+, 3H), 4.5 (q, 2H), 5.3 (5,2H), 7.5-8.3 (m, 4H), 9.0 (5, 1H).
  • 2
  • [ 1721-26-2 ]
  • [ 124797-01-9 ]
YieldReaction ConditionsOperation in experiment
99% With trichloroisocyanuric acid; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 16h;Inert atmosphere; DMF (0.047 ml, 0.605 mmol) and trichloroisocyanuric acid (2.95 g, 12.71 mmol) were added to a solution of ester <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> (1.000 g, 6.05 mmol) in DCM (7 ml) and resulted mixture was stirred 16 h at RT. Concentrated and purified on ISCO using 10-30% ethylactate in hexanes to give ethyl 2-(chloromethyl)nicotinate I in 99% yield (LCMS (M + H): 200). Ethyl 2-(chloromethyl)nicotinate I (100 mg, 0.501 mmol) and (5- amino-2-chlorophenyl)(morpholino) methanone (121 mg, 0.501 mmol) were dissolved in EtOH (5 ml) and AcOH (0.5 ml) and reaction mixture was refluxed overnight. Concentrated and purified on ISCO using 0-10% MeOH in DCM gave the desired product 17. Yield: 28%; 1H NMR (400 MHz, DMSO-d6) d 8.83 (dd, J = 4.9, 1.6 Hz, 1H), 8.19 (dd, J = 7.7, 1.6 Hz, 1H), 8.02 (dd, J = 8.9, 2.8 Hz, 1H), 7.97 (d, J = 2.6 Hz, 1H), 7.62 - 7.55 (m, 2H), 5.16 - 5.01 (m, 2H), 3.66 (d, J = 2.9 Hz, 4H), 3.55 (t, J = 5.0 Hz, 2H), 3.17 (dd, J = 6.4, 3.6 Hz, 2H); FABMS (M + H) calculated for CigHieClNsOs.H was 358.0953 found 358.0953; HPLC purity > 93 (% of AUC), tR = 9.85 minutes.
 

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