The Vespiary

The Hive => Tryptamine Chemistry => Topic started by: xxxxx on April 29, 2004, 07:08:00 AM

Title: nitroethene adds to indole
Post by: xxxxx on April 29, 2004, 07:08:00 AM

i once read that nitroethene adds to indole to form ethylnitro indole. refs from dictionary of organic compounds say nitroethene is formed by heating 2-nitro ethanol with some semi-exotic but getable compound to eliminate water. refs say 2-nitro ethanol is in turn formed by reacting nitromethane with formaldehylde. is this method known? if so, can someone provide details on conditions and yield.

Title: JOC 1980, 1185 is referenced by ...
Post by: ning on April 29, 2004, 08:19:00 AM

JOC 1980, 1185

is referenced by

https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-amt-enantiomers.pdf (https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-amt-enantiomers.pdf)

where they perform this operation with nitropropenes.

It sounds much like a Michael reaction.

https://www.thevespiary.org/rhodium/Rhodium/pdf/nitroethene.in.organic.synthesis.pdf (https://www.thevespiary.org/rhodium/Rhodium/pdf/nitroethene.in.organic.synthesis.pdf)

will have much of what you want to know.
In this paper, they used phthalic anhydride to dehydrate the nitroethanol. I imagine almost any anhydride would do. Perhaps even an azeotropic distillation. Who knows?

Lastly, you may have been looking for this:

https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.indole.nitroethylation.pdf (https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.indole.nitroethylation.pdf)

have fun. use ye olde search engine.

Title: 2-nitroethanol
Post by: gsus on April 29, 2004, 03:13:00 PM

another method, the formaldehyde/nitromethane way:

http://www.orgsyn.org (http://www.orgsyn.org)

search for 2-nitroethanol. CV 5, 833. with equimolar amts of HCHO and CH3NO2, one gets a 9% yield. large excess nitromethane necessary.

Title: Ugh!
Post by: ning on April 29, 2004, 08:01:00 PM

Yes, methinks NaNO2 + ethylene chlorohydrin is definitely the way to go.