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18th January 2017 @ 21:32

Synthesis of NA-03-01.png


Reagents

Equivalents

Quantity
 (mg / mL)

mmol

Molecular Weight g/mol

2-chloro-6-hydrazineylpyrazine

1

200 mg

1.38 mmol

144.56

2-(pyrrolidin-1-yl)benzaldehyde

[NA-02-02-PURE]

1

240 mg

1.38 mmol

175.23

EtOH (proof.)

-

9.6 mL

2.20 mmol

 











Procedure

To a stirred solution of 200 proof EtOH (9.6 mL) 2-(pyrrolidin-1-yl)benzaldehyde (240 mg, 1.38 mmol, 1 eqv.) was diluted in a 50 mL RBF. This was followed by the addition of 2-chloro-6-hydrazineylpyrazine (200 mg, 1.38 mmol, 1 eqv.). The mixture was left to react for approx. three hours at room temperature while stirring. The reaction was monitored with the use of TLC analysis to check for completion-two plates. The reaction mixture [NA-03-01] (E)-2-chloro-6-(2-(2-(pyrrolidin-1-yl)benzylidene)hydrazineyl)pyrazine was later rotary evaporated and weighed (424.8 mg, 1.41 mmol, 102% yield). A sample of [NA-03-01] was obtained for 1H NMR analysis with the use of CDCl3 solvent and for TLC analysis (50% EtOAc/pet. Ether).

 

Notes:

The mixture looked yellow orange at the beginning and gradually got darker till it became a maroon red at the end of experiment.

At the start:

solution-10:33am.JPG
   
solution-10:40am.JPG
   
solution-11:52am.JPG

 

Rotary evaporation of RM:

 

14-11-IMG_0550.JPG
 
14-11-IMG_0552.JPG
   
14-11-IMG_0553.JPG
   
14-11-IMG_0555.JPG

 


TLC PLATES

(1)

TLC NA-03-01 (1).JPG
       
TLC NA-03-01 (11).JPG


(2)

TLC NA-03-01 (2).JPG
       
TLC NA-03-01 (22).JPG


Rf values of solution mixture:

At 12:30 PM 

Rf(1)= 0.63  -but too concentrated so done again

Rf(2)= 0.61 – might have gone to completion 

Rf value of product [NA-03-01] NMR sample:  Rf= 0.59

 


NMR

NA-03-01.jpeg
Attached Files
Synthesis of NA-03-01.png
NA-03-01.jpeg
TLC NA-03-01 (2).JPG
TLC NA-03-01 (11).JPG
TLC NA-03-01 (1).JPG
TLC NA-03-01 (22).JPG
14-11-IMG_0550.JPG
14-11-IMG_0552.JPG
14-11-IMG_0553.JPG
14-11-IMG_0555.JPG
solution-10:40am.JPG
solution-10:33am.JPG
solution-11:52am.JPG