Author Topic: nitroethene adds to indole  (Read 1292 times)

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xxxxx

  • Guest
nitroethene adds to indole
« 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.

ning

  • Guest
JOC 1980, 1185 is referenced by ...
« Reply #1 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



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


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



have fun. use ye olde search engine.


gsus

  • Guest
2-nitroethanol
« Reply #2 on: April 29, 2004, 03:13:00 PM »
another method, the formaldehyde/nitromethane way:

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.


ning

  • Guest
Ugh!
« Reply #3 on: April 29, 2004, 08:01:00 PM »
Yes, methinks NaNO2 + ethylene chlorohydrin is definitely the way to go.