AMT from indole [pictures]

brain · Linguist Extraordinaire

i will make pictures in all steps of this synthesis! Smile

i want to make 1-(3-indolyl)-2-nitropropene-1 from :

http://www.erowid.org/library/books_online/tihkal/tihkal48.shtml

than reduce it on Al/Hg

DMF 1l :

indole 100g :

nitroethan 100g :

POCl3 250ml :

amonium acetate (or i will use n-buthylamine) :

------------------------

hawe anyone experience with this reaction?

jory · Tue May 17, 2005 8:00 pm

brain · Linguist Extraordinaire

and the statement :

jory · Tue May 17, 2005 8:23 pm

jory · Tue May 17, 2005 8:25 pm

brain · Linguist Extraordinaire

and what about Al/Hg reduction in thes case? will temp. be deadly for product? anyone done that before?

brain · Linguist Extraordinaire

I'm doing now aldehyde, now I rised temp to 40C and its about 30 min stirring, and no precipate is formed !!!! help ! what can I do to make it precipate...? i dont want to waste 25g of indole ... Sad

-mabey in this period of reaction, the precipate dont hawe to form? if it wont form, i will wait another 45 min, and add it to hipped ice, than add NaOH like in recepie.
[pictures will be later]

brain · Linguist Extraordinaire

after adding this solution to ice, the solution became a nice red-pink colour, clear solution, after adding NaOH, the colour changed to yellow, and after couple of minutes and adding ice the yellow precipate was formed ! now i'm filtrate this - it will take a while, when i will finish i will show you pictures Smile

btw~the addition of POCl3 to DMF was dropped in 10-15 min! the temp. dont rised abowe 10C, and adding to this solution a solution of indole+DMF was longer! about 30-50 min, ice bath is nececery !!

brain · Linguist Extraordinaire

this is the ampula with POCl3 , the top neck was braked with pliers :

25,75g of indole [cream white colour] :

weighted on normal weight ( +/- 10mg) :

adding 100ml od DMF to indole-indole imidietley dissolwe-yellow solution :

on ice bath, POCl3 is added in 0,5 ; 1 ; 5 ml portions to DMF - take~10min , temp. is easy to controll :

adding to POCl3+DMF, the indole+DMF solution (slight yellow), temp. is harder to control-but not so hard at all Smile

:

heating the solution to 40C, the yellow solution is darker, something like orange-yellow :

adding solution to ice , the solution become red :

adding NaOH, the solution is becoming yellow again :

than just filtrate precipates (water and ice was added to solution) , I dont like normal filtrating, think i will hawe to repar my wacum pump Wink

:

just wash with cold water, and dry on air :

--------

when it will be dry enough, i will weight it and tell the yeld Smile

brain · Linguist Extraordinaire

28,5g -that is wierd ! almoust 100% yeld? mabey i hawe to recrystalize it from DMF aq. ? [how much H2O and how much DMF?]

-mabey there are some salts [ NaI etc.?] But i think they will not bather in condensation with EtNO2

could anyone tell me proportions of condensation this aldehyde+EtNO2+n-buthylamine ? [i dont want to use large excess of EtNO2, instead i will use toluene i think] Smile

brain · Linguist Extraordinaire

i added 10ml EtNO2 + 4g aldehyde + 1ml n-butylamine

aldehyde didnt dissolwe in EtNO2, after adding n-buthylamine, colour of precipate changed on intensiw yellow, and solution is orange... mabey adding toluene will help the reaction?

how can I separate this aldehyde from nitrocompound ? [recrystalize from IPA?]
mabey someone know solubilitis this aldehyde and his nitro compound is different solwents [ipa, acetone, dmf] ?

brain · Linguist Extraordinaire

i now freezed it and got orange crystaline mass, that could be recrystalized i think, but i will try to reduce this not pure crystals :

Guest · Sun May 29, 2005 9:54 am

oh my,

Our first complete synth with pics!!!!!

Well done brain,
You have won the first ever complete photo synthesis award!

If you can do a quick write-up, then I will compile and publish it for you in the "write-ups forum'

This is a rare and wonderful treat brain,
Thankyou,

syn

brain · Linguist Extraordinaire

it will be complete when i reduce nitro compound with Al/Hg Smile

[i will do it toady-i think]

i dont know, but i think I could add to Al/Hg reactor - colution of nitrocompound+rest of aldehyde+EtNO2 whih not react , [just washed with water after adding] - i dont hawe wacum now-for getting rid of EtNO2, and freezing is not so efectiwe like in P2NP.

can i use Zn/Hg ? its less reducing agent, but reduction will be not so hot, and quick ...

i did the nitrocompound synthesis like in tikhal, the crystals widouth trituration MeOH crystals are orange, but i will reduce also orange crystals ... my aldehyde is wery slight yellow - not orange, like in tikhal, after recrysalization with 90% DMF / H2O solution, there formed slight orange-yellow needels [but with much lost! i think~25-30%] because of not knowed % [DMF/H2O] and amounts os solution per gram of aldehyde ...

---------

there are much infos. that i cant find and will be wery helpful, like solubilitis (solublke or not soluble) aldehyde, nitrocompound, in different solutions

Star-light · Blacklight bulb