Synthesizing 4-methylpyridine
Hello everyone. I will soon be attempting a big synthesis. but first I need a lot of 4-methylpyridine. I would rather not just buy it, and would find
it more fun to try to synthesize it.
First thing I wanna try is the Hantzch pyridine synthesis. I would use ethyl 3-oxopropanoate, acetaldehyde, and ammonia to make the dihydropyridine,
and then use acid to recover some ethanol and finally decarboxylate with basic copper carbonate.
The second involves making citrazinic acid with citric acid and urea in ethylene glycol and then using zinc/acetic acid to remove the hydroxyl groups
and convert the carboxylate into a methyl group. The carboxylate to methyl group is based on this procedure: https://sci-hub.st/https://doi.org/10.1135/cccc19480057
Also, I imagine that the dehydroxylation will likely work since zinc effectively dehydroxylates phenol into benzene, although I am unsure if the
nitrogen will interfere with the dehydroxylation.
Do you think either will work? Is there another way to synthesize 4-methylpyridine I'm not thinking of?
Attachment: zincreducinghydroxyl.pdf (321kB)
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