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20th November 2014 @ 15:03
Reaction Scheme:  Experimental Procedure:   see [blog=11264]Synthesis of (E)-4-((2-(6-chloropyridin-2-yl)hydrazono)methyl)benzonitrile (JS 10-1)[/blog]  To a solution of JS 10-1 (100 mg, 0.39 mmol, crude) stirred in CH2Cl2 (5.5 mL) was added Iodosobenzene diacetate (138.5 mg, 0.43 mmol). The reaction was stirred at room temperature and was monitored by TLC.  After one hour the reaction was complete as indicated by TLC (100% EtOAc). The reaction was washed with NaHCO3 (10 mL) and the layers separated. The water layer was extracted with DCM ( 3 x 10 mL) and the combined organic layers were then dried over MgSO4 before the solution was filtered and the solvents removed in vacuo.  The crude product was purified using flash column chromatography (from 100% EtOAc to 9/1 EtOAc /MeOH in a gradient) to yield compound 5 ( 90 mg, 91% yield % )  Risk Assessment :  [data]14053[/data] SMILES  ClC1=CC=CC(N/N=C/C2=CC=C(C#N)C=C2)=N1 to ClC1=CC=CC2=NN=C(C3=CC=C(C#N)C=C3)N21   InchI Strings InChI=1S/C13H9ClN4/c14-12-2-1-3-13(17-12)18-16-9-11-6-4-10(8-15)5-7-11/h1-7,9H,(H,17,18)/b16-9+ to InChI=1S/C13H7ClN4/c14-11-2-1-3-12-16-17-13(18(11)12)10-6-4-9(8-15)5-7-10/h1-7H NMR [data]14253[/data]
Attached Files
JS 11-1 .png