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Author: Subject: Hydrazine to Hydrazone question... please and thank you
German
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[*] posted on 19-4-2022 at 16:26
Hydrazine to Hydrazone question... please and thank you


Could someone help me clear up my confusion? I have a hydrazine group on a molecule and I thought I could turn it into a hydrazone, but after reading the literature I think I just got confused. The literature says in order to make a hydrazone you treat an aldehyde or a ketone with the chemical hydrazine and you get a hydrazone. Initially I think I read that backwards and concluded I could take my hydrazine GROUP (not the chemical) and treat it with like formaldehyde to get the group to turn into a hydrazone but after reading the literature again it seems I got confused.

So does anyone know if I could take my hydrazine group on my molecule and turn it into a hydrazone or anything else more useful? (I'm trying to get to nitrile, amide, or carboxylic acid).

Thank you.
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clearly_not_atara
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[*] posted on 19-4-2022 at 20:01


I think you can do it actually, you have to acylate the far end of the hydrazine somehow and then oxidize with activated DMSO.



[Edited on 04-20-1969 by clearly_not_atara]
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Fery
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[*] posted on 20-4-2022 at 04:10


Hi German, you are right. You can react your stuff with aldehyde/ketone. E.g. 2,4-dinitrophenylhydrazine (Brady's reagent) is used to determine aldehydes/ketones by creating their hydrazones with sharp melting points.



If there is a heaven, it seems not to be materially based. Does chemistry exist there and if yes, how does it look like? Are there good souls well supplied with laboratory equipment, glass, chemicals and information?
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njl
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[*] posted on 20-4-2022 at 05:29


Do you mean oxidizing your existing alkyl hydrazine into a hydrazone or condensing your hydrazine with a carbonyl to generate a hydrazone?



Reflux condenser?? I barely know her!
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German
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[*] posted on 20-4-2022 at 09:20


Quote: Originally posted by njl  
Do you mean oxidizing your existing alkyl hydrazine into a hydrazone or condensing your hydrazine with a carbonyl to generate a hydrazone?


Anything that gets me to hydrazone so if both those work then either one (I will try to find literature on those routes).

... And thank you to the other 2 responders. I will look into the mentioned possibilities. If it is as easy as reacting with a ketone/aldehyde then maybe instead of formaldehyde I can just dissolve in MEK and boil. I will look into all possibilties. Thank you.
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Triflic Acid
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[*] posted on 24-4-2022 at 07:59


Another option for you might be to reduce your hydrazine to an amine, then diazotize to make the alcohol, followed by oxidation to the ketone and creation of the hydrazine. But just mixing the aldehyde with straight hydrazine is faster.

Edit: Forgot to cite: Reduction of hydrazines to amines with aqueous solution of titanium(iii) trichloride

[Edited on 24-4-2022 by Triflic Acid]




There wasn't a fire, we just had an uncontrolled rapid oxidation event at the power plant.
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