N-formylation of primary amine

[Knoevenagel]

Hi

On basis of your knowledge how would you perform an N-formylation of amphetamine in the best possible way?

/ Knoevenagel

[Rhodium]

Reflux it with formic acid in toluene with a dean-stark water trap or reflux with ethyl formate.

[Knoevenagel]

Hi Rhodium

I´ve seen the post on amph -> meth on the Rhodium page(Ref: Phikal) page but this is for MDA. Does MDA have the same the reactivity towards formylation with HCOOH as the amph. Do you think the methylenedioxy-group interferes in some way with regards yields/reactivity?

/Knoevenagel

[Rhodium]

No, amphetamine should react exactly like MDA in this case.

[Knoevenagel]

RHODIUM!

Why formic acid, why not formyl chloride?. Any problems with this reactant as far as you concern? Shouldn´t this decrease reaction time, increase yield etc?

/ Knoevenagel

[terbium]

Perhaps because formyl chloride can be a bit difficult to acquire. I doubt that it can be purchased, it isn't stable enough. One would have to try to make it as needed.