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Nitrostyrenes to oximes with sodium dithionite

Started by Barium, April 18, 2003, 02:02:00 PM

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Hanswurst


arseholio

How about zinc dithionite? I reckon it could reduce to the amine?

arseholio

And what causes the discoloration of this reaction? Is the product come kind of bisulphite adduct od the ketone? Any suggestion for the reaction mechanics?

b6baddawg

im really not sure how to explain but how about using sodium sulfite? p2p not the oxime tho

lullu

Quote from: Hanswurst on July 24, 2016, 09:55:08 AM
Does not work, extremely low yield.

Thanks for reporting Hans!
can you go a bit into detail I assume you reduced some nitropropene to the alleged oxime followed by Mg reduction?
Did you isolate it in between?
Just because you are not paranoid does not mean they are not after you.

arseholio

Quote from: b6baddawg on July 24, 2016, 03:49:48 PM
im really not sure how to explain but how about using sodium sulfite? p2p not the oxime tho

Why in the earth one would  want to get rid of the nitrogen which has been placed there in the first hand?

arseholio

Quote from: lullu on July 24, 2016, 04:59:22 PM
Quote from: Hanswurst on July 24, 2016, 09:55:08 AM
Does not work, extremely low yield.

Thanks for reporting Hans!
can you go a bit into detail I assume you reduced some nitropropene to the alleged oxime followed by Mg reduction?
Did you isolate it in between?

Is this just parroting Vitus Verdegast's opinion? AB2 did trials - he noticed color change. So there must be some reaction. What is it? Yellowish flakes were formed at some point. I reckon these could be the nitronate. So is there anyone who could do some trials with pictures?

Zippy

Quote from: arseholio on July 24, 2016, 05:25:39 PM
Quote from: b6baddawg on July 24, 2016, 03:49:48 PM
im really not sure how to explain but how about using sodium sulfite? p2p not the oxime tho

Why in the earth one would  want to get rid of the nitrogen which has been placed there in the first hand?

It would be the goal if you wanted to make MDMA & not MDA.

Hanswurst

Did it twice, cold and hot and both yields were lower than 10 percent, I did distill and reduce with Na afterwards.
Barium seems to be a dipshit.

arseholio

I think the end product could be some kind of adduct or Na-salt. It should be tried again and afterwards hydrolyzed perhaps with HCl. It's clear there is a reaction. But without any HPLC or GC-MS verification, this is just guesstimating. Is there anyone willing?