Don’t get me wrong, I love Organic Syntheses, but sometimes the lack of a proper rationale is frustrating. In all likelihood, we will never know how this reaction was conceived. No, it is not a misprint, I have triple-checked it.



Org. Synth. 1963, Coll. Vol. 4, 451-453. (Available here.)

How do you think the discussion went? “OK guys, we are going to need about 70 grams of 5-ethyl-2-methylpyridine. What do you say? Heat some acetaldehyde with ammonia, perhaps with a buffer or something? Just a hunch.”

What is the mechanism? 🙂