I looked, but did not find.
In one version of tryptamine synthesis, oxalyl chloride is condensed with indole, then the stuff alkylates some amine to give this (I don't know what it's called)
Molecule:
intermediate ("c1nc2ccccc2c1C(=O)C(=O)N(C)C")
Which is then reduced with LiAlH4, usually. Every reaction on beilstein does this. Maybee some bee has used the clemenson reduction also, I do not know.
What I would like to know is whether a Wolff-Kishner reaction would remove those carbonyls, or reaction conditions would destroy the tryptamine. (Pictet-Spengler, Lili?
Or something?)
I guess if acidic conditions cause that, it would be a strike against the Clemenson. But Wolff-Kishner is basic. Any threads here on this matter already? UTFSE again?