I would like to know how to obtain the following molecule, whose technical name should be something like N,N-dimethylindol-3-ylglyoxylamide (let's call it DMIG for short)


One of the constraints being that I'd like to limit myself to compounds that are relatively easy/cheap (and, of course, legal) to find.

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I figured out that indole (A) may be a good starting point. Its very reactive spot on position 3 would make an electrophilic aromatic substitution likely to take place there.

Then, oxalyl dichloride (B) and dimethylamine (C) would be good candidates to construct the "dimethylglyoxylamide" leg.

And... my technical knowledge stops right there. Would it be possible to obtain DMIG from compounds A, B and C by "simply" putting them in solution in an adequate way? As a layman in experimental chemistry, it seems to me that the most reactive spots in the system are the position 3 of the indole, the chlorine endings of the oxalyl dichloride and the N-H bond in the dimethylamine. If this premise is correct (which may not be the case), then I have the intuition that not much would be required to lead to the formation of DMIG.

What process would you suggest? What other substances may be necessary? Are there other paths or more practical starting points for this synthesis?

Thanks in advance

  • $\begingroup$ Add an ethereal solution of indole (1 equiv) slowly to ethereal oxalyl chloride (1.1 equiv). Substitution occurs at the 3-position of indole. The acyl chloride is yellow and crystalline. Dissolve acyl chloride in a solvent and react with the amine. Welcome to SE! $\endgroup$ – user55119 Mar 18 '18 at 1:11
  • $\begingroup$ I have improved confusing name "N,N-dimethylindol-3-ylglyoxylamide" to N,N-dimethyl-2-(indol-3-yl)glyoxylamide (in the title), correct preferred IUPAC name would be 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide. Also note that your formulæ have "typo", miss one degree of unsaturation in indole. $\endgroup$ – mykhal Jan 13 '19 at 13:54

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