5-MeO-MRT from melatonin

[periannath]

I checked TFSE and didn't find anything so....
I think found a simple way to make 5-MeO-MRT from Melatonin. All you have to do is react it with X₂ or a hypohalite (pool shock is Ca(ClO)₂) and then NaOH.(keep it cold) purify and treat with your favorite alkyl halide.
BTW my organic chemistry knowledge is somewhat limited as everything I know about it I have learned in the last month and a half. So this may seem stupid but..

How do I stop quarternary salts from forming?

[Rhodium]

What is 5-MeO-MRT?

[periannath]

R is any alkyl group

[Lilienthal]

Sorry, but that doesnt work. You might get *something*, but certainly not N-alkyl-N-methyl-5-methoxy-tryptamine.

[periannath]

Why? it's just a hofmann rearrangement.
PLease enlighten me. I'm trying to learn.

[Lilienthal]

For a Hofmann rearrangement you need an unsubtituted amide because the reaction mechanism is:

R-CONH₂ ^__> R-CONHBr ^__> R-N=C=O (isocyanate) ^__> R-NH-COOH ^__> R-NH₂

The isocyanate simply can't accomodate a second alkyl group.