Author Topic: Nitrostyrenes to oximes with sodium dithionite  (Read 2988 times)

0 Members and 1 Guest are viewing this topic.

Offline Hanswurst

  • Subordinate Wasp
  • ***
  • Posts: 161
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #20 on: July 24, 2016, 09:55:08 AM »
Does not work, extremely low yield.

Offline arseholio

  • Larvae
  • *
  • Posts: 45
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #21 on: July 24, 2016, 10:48:21 AM »
How about zinc dithionite? I reckon it could reduce to the amine?

Offline arseholio

  • Larvae
  • *
  • Posts: 45
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #22 on: July 24, 2016, 10:51:02 AM »
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?

Offline b6baddawg

  • Subordinate Wasp
  • ***
  • Posts: 148
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #23 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

Offline lullu

  • Dominant Wasp
  • ****
  • Posts: 347
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #24 on: July 24, 2016, 04:59:22 PM »
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?

Offline arseholio

  • Larvae
  • *
  • Posts: 45
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #25 on: July 24, 2016, 05:25:39 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?

Offline arseholio

  • Larvae
  • *
  • Posts: 45
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #26 on: July 24, 2016, 05:49:06 PM »
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?

Offline Zippy

  • Dominant Wasp
  • ****
  • Posts: 358
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #27 on: July 24, 2016, 06:08:08 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.

Offline Hanswurst

  • Subordinate Wasp
  • ***
  • Posts: 161
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #28 on: July 26, 2016, 03:34:14 PM »
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.

Offline arseholio

  • Larvae
  • *
  • Posts: 45
Re: Nitrostyrenes to oximes with sodium dithionite
« Reply #29 on: July 26, 2016, 07:08:06 PM »
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?