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2nd March 2018 @ 13:22

Method:

2-chloro-6-hydrazinopyrazine (A) (100.00 mg, 0.70 mmol, 1.00 equiv.) was dissolved in EtOH (10 mL) forming a yellow solution, to which 4-carboxybenzaldehyde (B) (113.5.0 mg, 0.76 mmol, 1.1 equiv.) was added. The yellow solution was stirred for five minutes at room temperature, with B not seeming to dissolve to any appreciable degree. The reaction was stirred for a further 2.5 hours and was monitored by TLC. Solvent systems included 1:9 and 3:7 Ethyl acetate: PET ether, as well as dichloromethane with all of them little to no evidence of product forming – it could be that TLC is not an appropriate method for monitoring this reaction. The reaction mixture was filtered under vacuum to give 2-chloro-6-(2-hydrazinyl(4-carboxybenzylidene))pyrazine) as a pale pink powder (108.6 mg, 56.9%) which was characterised by IR and 1H NMR. Remaining product in the filtrate was also recovered in vacuo, with no appreciable yield. The product was characterised by IR and 1H NMR, the latter displaying a clear and large excess of 4-carboxybenzaldehyde starting material.

 

 


Attached Files
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4-carboxy hydrazone 1H NMR.pdf