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20th March 2018 @ 14:09

Method:

2-chloro-6-hydrazinopyrazine (100.0mg, 0.69 mmol, 1.00 equiv.) was partially dissolved in EtOH (~10 mL) forming a yellow solution. 2-hydroxybenzaldehyde (0.1 mL, 0.958 mmol, 1.2 equiv.) was then added giving a clear yellow solution. The mixture was stirred for 2 hours before being heated to 72°C for 5 minutes and became progressively slightly darker in colour; it was monitored by TLC (9:1 PET ether: Ethyl acetate) until completion. The mixture was allowed to cool, producing yellow needle like crystals (21 mg) which were isolated by filtration, collected and analysed by 1H NMR and IR spectroscopy. Spectra were inconclusive, but it was determined that the crystals were not the desired product. The filtrate was collected and solvent removed under vacuum to give an orange powder, 2-chloro-6-(2-hydrazinyl(2-hydroxybenzylidene)pyrazine) (142.6 mg). This was characterised by IR and 1HNMR, showing presence of desired product and the unknown compound previously isolated.

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