Author Topic: Anyone heard of this Nitro reduction?  (Read 10075 times)

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karel

  • Guest
Hello Sunlight, have you tried those ...
« Reply #20 on: January 08, 2003, 01:20:00 PM »
Hello Sunlight,
have you tried those conditions

Post 245040

(Rhodium: "O Leminger's Phenethylamines - posted by Karel", Novel Discourse)
?

Sunlight

  • Guest
Hi Karel
« Reply #21 on: January 09, 2003, 10:40:00 AM »
As I've posted in that thread, I discovered it recently, I'll try it soon, I promise it to you, but I doubt to use methanol or 96 ethanol (with denaturants)... I hope it won't be important.
Thanks for your research.

Sunlight

  • Guest
Excuse me
« Reply #22 on: February 27, 2003, 04:13:00 PM »
I thought that the Zn/An formate rdxn of nitro compounds was something similar to the classic Zn acetic one. Then Rhodium posted another reference wich uses zinc and hidrazinium monoformate, very similar to this one, so I decide to try it and see what happens.
Initially I checked adding Zn to a solution of ammonium formate and methanol, and it makes nothing. Then I added nitromethane and zinc to methanol and then added the formate, and as sonn as it came in solution started a energic, exhothermic and effervescent reaction. The same, but immediatly, happened when the zn was added to a solution of nitromethane and ammonium formate in methanol, disappearing completely the Zn, wich was not pretreated with diluted HCl (but good quality one).
In conclusion I was wrong, but my doubts about the amount of reactants still persist. They use 0.6 mmol of Zn and 0.8 mmol of formate to reduce 0.5 mmol of nitrocompound, my best numbers are that the formate could decompose giving 0.8 mmol of H2 and the Zn could react with the NH3 producing 0.6 mmol of H2 more, 0.14, but it is necessary 0.15 for a 100 % efficiency. Furthermore, when formic acid is used instead of the formate, the Zn disappears, so I think it reacts forming the formate.
Any light about the mechanism of the reaction ?

Antibody2

  • Guest
sunlight - while pondering the ratios you...
« Reply #23 on: June 11, 2003, 03:35:00 PM »
sunlight - while pondering the ratios you mention i am further intrigued by the massive XS of HCOOH they use in the proceedure, 48mmol. 8X the amount of ammonium formate they advocate using. Surely that has got to be a typo??

starlight - i agree the formic acid should probably be added slowly, it describes this as a room temp reaction, not a reflux reaction. maybe  even using a water bath?

anybees besides Barium have anything to report on this rxn? :)  especially using formic acid instead of the salt

starlight

  • Guest
formic acid worked fine
« Reply #24 on: June 16, 2003, 02:43:00 PM »
Formic acid worked fine when reducing 2,4,5-Trimethoxy Phenyl-2-Nitropropane to TMA-2. Can't remember exact yields as it was months ago, but they were good enough to call a success.

Antibody2

  • Guest
do you remember the ratios of formic used?
« Reply #25 on: June 20, 2003, 10:17:00 PM »
do you remember the ratios of formic used?


starlight

  • Guest
xs as described
« Reply #26 on: June 27, 2003, 06:01:00 AM »
the procedure has only been tested using the ratio of reactants described in the original paper.