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Nice work!

By the sound of your work up, there would not be much leftover amide asa, or salicylic acid

Did you recover the amide separately? Dilute Hcl and bicarbonate washes of the original DCM will remove any dmt, nmt, asa, and salicylic acid.

It would be cool to hydrolyze to recover the NMT, but amides are dang rocks, even boiling in NaOH won't do it.

In my experiments hydrolyzing a very similar molecule, 5-meo-n-aceťyltryptamine (melatonin), typical methanolic NaOH did not work, neither ethanol or isopropyl. The rxn was just too slow, it would take around 6hr to complete, but boiling for that long causes decomposition of the tryptamine ( argon atmosphere would help) doing it in higher bp alcohols like butanol gave completion in only 1hr, a bit of antioxidant thrown in helps with decomp, I got decent yields of around 65%. Butanol is stinky though and hard to acquire, I'd like to test out ethylene glycol or glycerol, at 100C, they may work just fine.

This is why carbamates appeal to me too, it is much more reversible

Reduction of course, would be fun, but you have the problem of amide being stable as a rock again! Needs very violent reagents to reduce!

<blockquote data-quote="Mindlusion" data-source="post: 3601453" data-attributes="member: 5911">Nice work! By the sound of your work up, there would not be much leftover amide asa, or salicylic acidDid you recover the amide separately? Dilute Hcl and bicarbonate washes of the original DCM will remove any dmt, nmt, asa, and salicylic acid.It would be cool to hydrolyze to recover the NMT, but amides are dang rocks, even boiling in NaOH won&#039;t do it.In my experiments hydrolyzing a very similar molecule, 5-meo-n-aceťyltryptamine (melatonin), typical methanolic NaOH did not work, neither ethanol or isopropyl. The rxn was just too slow, it would take around 6hr to complete, but boiling for that long causes decomposition of the tryptamine ( argon atmosphere would help) doing it in higher bp alcohols like butanol gave completion in only 1hr, a bit of antioxidant thrown in helps with decomp, I got decent yields of around 65%. Butanol is stinky though and hard to acquire, I&#039;d like to test out ethylene glycol or glycerol, at 100C, they may work just fine.This is why carbamates appeal to me too, it is much more reversibleReduction of course, would be fun, but you have the problem of amide being stable as a rock again! Needs very violent reagents to reduce!</blockquote>

[QUOTE="Mindlusion, post: 3601453, member: 5911"] Nice work! By the sound of your work up, there would not be much leftover amide asa, or salicylic acid Did you recover the amide separately? Dilute Hcl and bicarbonate washes of the original DCM will remove any dmt, nmt, asa, and salicylic acid. It would be cool to hydrolyze to recover the NMT, but amides are dang rocks, even boiling in NaOH won't do it. In my experiments hydrolyzing a very similar molecule, 5-meo-n-aceťyltryptamine (melatonin), typical methanolic NaOH did not work, neither ethanol or isopropyl. The rxn was just too slow, it would take around 6hr to complete, but boiling for that long causes decomposition of the tryptamine ( argon atmosphere would help) doing it in higher bp alcohols like butanol gave completion in only 1hr, a bit of antioxidant thrown in helps with decomp, I got decent yields of around 65%. Butanol is stinky though and hard to acquire, I'd like to test out ethylene glycol or glycerol, at 100C, they may work just fine. This is why carbamates appeal to me too, it is much more reversible Reduction of course, would be fun, but you have the problem of amide being stable as a rock again! Needs very violent reagents to reduce! [/QUOTE]