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20th March 2018 @ 14:12

Method:

2-chloro-6-hydrazinopyrazine (100.0mg, 0.69 mmol, 1.00 equiv.) was partially dissolved in EtOH (~12 mL) forming a yellow suspension. 4-nitrobenzaldehyde (117.0 mg, 0.77 mmol, 1.1 equiv.) was then added partial dissolution. The mixture was stirred for 10 minutes before being heated to 30°C to aid solubility. The yellow suspension was stirred and heated for a further 2 hours and 40 minutes and became progressively deeper orange coloured; it was monitored by TLC (9:1 PET ether: Ethyl acetate) until completion. The solid was filtered under vacuum to give 2-chloro-6-(2-hydrazinyl(4-nitrobenzylidene)pyrazine) as a yellow powder (105.6 mg, 55%). This was characterised by IR and 1H NMR. 


Attached Files
20:3-3.png
1H NMR 4-nitro imine formation zoomed.pdf
1H NMR 4-nitro imine formation unzoomed.pdf