German
Harmless
Posts: 44
Registered: 13-5-2009
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
clearly_not_atara
International Hazard
Posts: 2787
Registered: 3-11-2013
Member Is Offline
Mood: Big
|
|
I think you can do it actually, you have to acylate the far end of the hydrazine somehow and then oxidize with activated DMSO.
|
|
|
Fery
International Hazard
Posts: 1015
Registered: 27-8-2019
Location: Czechoslovakia
Member Is Offline
|
|
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.
|
|
|
njl
National Hazard
Posts: 609
Registered: 26-11-2019
Location: under the sycamore tree
Member Is Offline
Mood: ambivalent
|
|
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!
|
|
|
German
Harmless
Posts: 44
Registered: 13-5-2009
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
Triflic Acid
Hazard to Others
Posts: 486
Registered: 27-9-2020
Member Is Offline
Mood: Slowly Oxidizing into Oblivion
|
|
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.
|
|
|
Texium
|
Thread Moved
25-4-2022 at 06:10 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
