Help with name (and preparation) of this compound

I haven't got chemdraw or anything so a simple description will have to do..

I want to look into the preparation of the compound comprising skatole with a -NO2 group replacing one of the hydrogens of the 3-methyl group: "Indole-3-nitromethane(?)" - but searching under this name gives nothing, nor does any other variant i can think of.

Can anyone suggest the common name for this molecule so that i may have more luck looking up its synthesis (from indole, indole-3-carbinol?). Or if someone could point me towards a reference for the synthesis that would be better still!! Thanks

Quote:

Originally posted by sonogashira I haven't got chemdraw or anything so a simple description will have to do.. I want to look into the preparation of the compound comprising skatole with a -NO2 group replacing one of the hydrogens of the 3-methyl group: "Indole-3-nitromethane(?)" - but searching under this name gives nothing, nor does any other variant i can think of. Can anyone suggest the common name for this molecule so that i may have more luck looking up its synthesis (from indole, indole-3-carbinol?). Or if someone could point me towards a reference for the synthesis that would be better still!! Thanks

What you have is 3-(nitromethyl)-1H-indole.

This may be accessible via gramine. See http://en.wikipedia.org/wiki/Gramine.

Indoles with this substitution pattern were prepared (page 20) in this patent: http://www.pat2pdf.org/patents/pat5597922.pdf. The reaction scheme is attached. You have to read beyond page 20 to find the actual examples where these compounds were prepared.

Indole-2-carboxylic acid compounds such as the one pictured are readily decarboxylated under acidic conditions.

There are likely many other ways to make your compound but this should give you a start.





[Edited on 28-7-2008 by Ritter]

Thanks for the suggestion, although it seems a little too involved for me. I got quite excited when i saw a paper concerning a one step R-OH to R-NO2 transformation (thinking of starting from indole-3-carbinol) but then i read this thread and realized it was all crap!

Looks like the idea will have to be abandoned. It doesn't appear to be a very common chemical from what i can tell: acs and rsc searches gave virtually nothing

Thanks again