(Stranger)
04-29-04 07:08
No 503744
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.
(acetaminophanatic)
04-29-04 08:19
No 503757
JOC 1980, 1185
is referenced by
https://www.rhodium.ws/pdf/nichols/nicho
where they perform this operation with nitropropenes.
It sounds much like a Michael reaction.
https://www.rhodium.ws/pdf/nitroethene.i
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.rhodium.ws/pdf/tryptamine.in
have fun. use ye olde search engine.
I've been chased by both cops and robbers. So what does that make me?
(Hive Bee)
04-29-04 15:13
No 503815
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.
http://www.maps.org
(acetaminophanatic)
04-29-04 20:01
No 503871
Yes, methinks NaNO2 + ethylene chlorohydrin is definitely the way to go.
I've been chased by both cops and robbers. So what does that make me?