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20th November 2014 @ 11:34

Note: See Synthesis of (E)-4-((2-(6-chloropyridin-2-yl)hydrazono)methyl)benzonitrile (JS 6-1) for previous problems trying to synthesise the desired E isomer . 


Reaction Scheme 

Experimental Procedure 

JS 4-1 [see - Synthesis of 2-chloro-6-hydrazinylpyradine (JS 4-1) ] (1.005 g, 7 mmol) was stirred into a solution of ethanol (100 mL). 4-cyanobenzaldehyde (0.92 g, 7 mmol) was added and the reaction was stirred at refux for 2 hours.

TLC (Hexane/EtOAc - 70/30) indicated that the reaction was complete. 

The solvents were removed in vacuo and the crude was used in the next reaction (1.88 g, 104 % ) 

Risk Assessment 

JS 10-1.docx

SMILES 

 

ClC1=CC=CC(NN)=N1 

and

[H]C(C1=CC=C(C#N)C=C1)=O

to

ClC1=CC=CC(N/N=C/C2=CC=C(C#N)C=C2)=N1

 

InChI Strings 

InChI=1S/C5H6ClN3/c6-4-2-1-3-5(8-4)9-7/h1-3H,7H2,(H,8,9)

and

InChI=1S/C8H5NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,6H

to

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+


NMR 

JS 10-1 .png
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Attached Files
JS 10-1.png
JS 10-1.docx
JS 10-1 .png