I'm certain that I must be missing something here, but alas I will ask anyhow.. why do all the syntheses for DMT from indole-3-acetic acid listed on rhodium follow the scheme: ester formation, aminolysis w/dimethylamine, reduction of amide. According to the syntheses, the aminolysis step takes 48 hours and I am quite impatient. If someone were to go this route, would the addition of an alkali alkoxide not accelerate this process tremendously?
However, my real question is why a scheme analogous to shulgin's indole/oxalyl chloride synthesis from tihkal would not work. What I mean is simply reacting the acid with PCl3 to form an acyl halide, indole-3-acetyl chloride. Reacting this acid chloride with dimethylamine in dry ether (as per shulgin w/glyoxlyl chloride.) And finally, reducing the amide to the desired amine. Yes, this is the same number of steps but I don't believe the formation of the amide from an acyl halide would take 48 hours as it does with an ester.
Also, would it be possible to simply reduce the acid to tryptophol, react tryptophol with an acid halide to displace the hydroxyl with a halogen, followed by aminolysis w/dimethylamine to displace the halogen and form the amine.
I realize all of this is obvious and straight-forward chem and they would already be established routes if they worked; therefore I am more interested in *why* these traditional methods do not work..