verification of reduction methods

joe_aldehyde · huxleys associate

please do suggest some reduction methods you want me to try for phenyl-2-nitropropene. i have thought of NaBH4 followed by Zn/HCOOH or Zn/HCl. also a CTH using HCOOH (does Calcium Formiate work well as a hydrogen donor, too?) would be possible. i also have quite a bit of 10% Pd/C from Degussa which i would like to use in a catalytic hydrogenation with molecular H2 generated by dissolving metal in mineral acid or NaOH). if i get some overhead stirring equipment, i would also try urushibara. or urushibara in the ultrasound bath? post away, bees!

any method you suggest will be tested along with a detailed writeup.

IndoleAmine · Dreamreader Deluxe

Just search around and compare by yourself, usually the yield in percent is given along with experimental data around here... Wink

joe_aldehyde · huxleys associate

i'M not looking for the best reduction method, all i want to do is some verification in order to see if there are still as much faked writeups around.

jackoozzi · specialist

Thats a great offer thanks joe

I cant think of any off hand but i am sure some of our other bees will

Star-light · Blacklight bulb

loki · guinea pig

waaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa :'(

joe_aldehyde · huxleys associate

this is not just about discovering fakes but also VERIFICATION of the general procedure. sometimes intermediate steps are missing etc. i'm trying to solve problems like this before anybody attempts them and runs into trouble. i see no insult to anybody in my offer. if i'd like to do that, i'd certainly go yelling at the respective author telling him that his writeup is crap. but i'm not like that, since i don't really know it before i cook it up! werd

starlight- don't worry. i know somebody that doesn't learn from his failures, and it's not me Smile

mk-1 · Tue May 31, 2005 9:49 pm

joe aldehyde,
Please if u have the chance, try the following :
indole + oxalyl chloride + alkylamine -> indolglyoxylamide.
indolglyoxyl amide reacted with phosphorus oxychloride should yield a chlorinated product where the amide and ketone O's were.
Reduction of this with NaBH4 should yield di-alkyl-tryptamine.
This was suggested to me by some1 in the know, and there are refs if u want them. I dont have too much NaBH4 to spare, so if u could verify this it owuld be most nice!

loki · guinea pig

that's one of the oldest published routes on the internet i believe. the oxalyl chloride reaction gets pretty hot, and iirc, is a watched chem anyway.

mk-1 · Wed Jun 01, 2005 11:58 am

Loki, dont know what is IIRC, but i do know that ive never seen anything on the net about the reduciton of the glyoxylamide to the tryptamine with anything besides LAH.
if u have, let me know... would be interesting.

loki · guinea pig

iirc=if i remember correctly

um... yeah i've never heard of anything other than LAH either. but other things might work, lots of other things. best bet is to search for an analogous reaction and find writeups which mention the use of other reducing agents.

joe_aldehyde · huxleys associate

i'd love to try your rxn, mk-1, but right now i'm reserving myself to available phenethylamine substrates, hence the thread in THIS subforum Smile

jory · Wed Jun 01, 2005 7:31 pm

amenselah · Sun Sep 25, 2005 3:35 am

why not the Al/hgcl2?

anime · Sat Oct 01, 2005 10:26 pm

HgCl2 is toxic as fuck, and working with is constantly is something one would not rather do.
the Al/Hg reductions work magnificently but there is the issue of disposal of toxic sludge and exposure. Also work up is a bitch.

Btw (JA)Urushibara will reduce nitro groups at 1 atm.