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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: rolnor on October 20, 2020, 01:24:06 PM

Title: DMF+amine
Post by: rolnor on October 20, 2020, 01:24:06 PM

I wonder if DMF can formylate a benzylic primary amine if heated to 110°C ? I made the reaction in this solvent and got some high-Rf material. I can se this high-Rf material even if I dont use DMF so I dont think its a problem but I am not 100% sure, what do you think, is trans-amidation possible?

Title: Re: DMF+amine
Post by: AWK on October 20, 2020, 01:56:31 PM

https://pubs.rsc.org/en/content/articlehtml/2018/ra/c8ra04985h

Title: Re: DMF+amine
Post by: rolnor on October 20, 2020, 02:09:20 PM

Thanx!

It seems they use methylbenzoate as catalyst for the formylation of amines so in my case this will not happen, they would not add methylbenzoate if its not necessary?

Title: Re: DMF+amine
Post by: wildfyr on October 20, 2020, 02:16:17 PM

isolate and check by FTIR, an amide or an aldehyde will be very obvious.

Title: Re: DMF+amine
Post by: rolnor on October 20, 2020, 04:55:05 PM

I dont have IR unfortunatley.
They use microwave heating, it does not say how warm.
I will check tomorow on TLC if the new spot is the same with and without DMF, I have to high Rf now so I can not judge.