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20th November 2014 @ 15:03

Reaction Scheme: 


Experimental Procedure: 

 see Synthesis of (E)-4-((2-(6-chloropyridin-2-yl)hydrazono)methyl)benzonitrile (JS 10-1) 

To a solution of JS 10-1 (100 mg, 0.39 mmol, crude) stirred in CH2Cl(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 :

 

JS 8-1.docx

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

JS 11-1 .png
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JS 11-1 .png