The Vespiary

The Hive => Methods Discourse => Topic started by: Knoevenagel on April 04, 2002, 02:56:00 AM

Title: N-formylation of primary amine
Post by: Knoevenagel on April 04, 2002, 02:56:00 AM

Hi

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

/ Knoevenagel

Title: N-formylation
Post by: Rhodium on April 04, 2002, 08:15:00 AM

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

Title: MDA v. amph
Post by: Knoevenagel on April 04, 2002, 07:56:00 PM

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

Title: mda/amph
Post by: Rhodium on April 05, 2002, 12:18:00 AM

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

Title: formyl chloride?
Post by: Knoevenagel on April 06, 2002, 03:22:00 AM

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

Title: Formyl chloride.
Post by: terbium on April 06, 2002, 04:33:00 AM

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.