[kriggy]

Hello, Im looking for a way to convert aromatic amino group into hydrazino group. As far as I know, the usual method is to diazotate and reduce using Na₂SO₃, this method however is not working for me (giving totaly different product). I´ve tried SnCl₂ reduction of diazonium salt and it worked but there is quite a lot of another products. I also tried diazotation, then condensation with malononitrile and then hydrolyzis of the product in acidic enviroment but the compound is practicaly insoluble in water or diluted acids and in concentrated acids there is also quite a mess.

I couldnt find anything in literature regarding the reduction except for electrochemical reactions, do you have any ideas/ papers/experience regarding this topic?

THank you very much

[Enthalpy]

Still no answer? Then here are my 2 cents - apologies in advance if I misunderstood, maybe it encourages better answers.

Do you want to convert into ?

In rocket amounts, and starting rather from methylamine or dimethylamine, the synthesis of hydrazine proceeds with chloramine.

[kriggy]

Thats basicaly it, the benzene ring is substitued in my case. Do you have a literature link about the reaction you are talking about? I think I figured it out on monday, reducing the diazonium salt with SnCl₂ works fine on low temperature on some of my combounds but Im looking for another options anyway.

Thanks for your reply

[Enthalpy]

https://hal.archives-ouvertes.fr/hal-00397543/document
their topic in 2009 may have been to have the chlorine at the more substituted amine (not the ammonia) to limit the number of side reactions.

I believe (not sure) that mass production of Mmh and Udmh still follows the Olin-Raschig process (1906)
https://en.wikipedia.org/wiki/Olin_Raschig_process
https://en.wikipedia.org/wiki/Unsymmetrical_dimethylhydrazine
https://en.wikipedia.org/wiki/Chloramine

I got the references over Google
MMH synthesis
and
hydrazine chloramine

I believe we'd all like to keep you here, so you'll take the adequate precautions, will you?

[kriggy]

Thank you for references, I wasnt realy sure what to look for except the chloramine  so thats why I asked you. Well, most likely I will not run this procedure since the SnCl2 reduction is somehow working and now its just about playing with conditions for different substrates I use but be asure I will take any precautions that are necessary if I will do the chloramine reaction.