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20th March 2018 @ 14:06

Method:

2-chloro-6-hydrazinopyrazine (A) (100.00 mg, 0.70 mmol, 1.00 equiv.) was dissolved in EtOH (10 mL) forming a bright yellow solution, to which 2,4-dimethoxybenzaldehyde (B) (126 mg, 0.76 mmol, 1.1 equiv.) was added. The reaction was stirred for a further 3.5 hours and was monitored by TLC. During this time, a yellow precipitate formed. The reaction mixture was filtered under vacuum to give 2-chloro-6-(2-hydrazinyl(2,4-dimethoxybenzylidene))pyrazine) as a yellow powder (59.1 mg, 29.2%) which was characterised by IR and 1H NMR. Remaining product in the filtrate, a dark orange oil, was also recovered in vacuo (98.1 mg, 48.4%). TLC of the filtrate showed a mixture of many compounds which proved very difficult to separate using a silica column, so the filtrate was discarded.

Attached Files
20:3-1.png
1H NMR 2,4-dimethoxy hydrazone formation.pdf