Assume that you have N,N-dimethylbenzamide (C9H11NO). Is it possible to convert it into N-methylabenzamide (C8H9NO) in one or two steps?
One of my professors thought it is feasible while another one told me that it is infeasible. I tried this controversial reaction on a similar system to the above for 3 months in the early 1980s but it did not work. Within the past 3 decades, have you heard of anyone succeeding in carrying out a similar reaction? Thanks in advance.
Thank you a lot Dr. Adel for your note. I corrected the unfortunate mistake in the question. All the best.
You can use the transamidation strategy. I think reaction of N,N-dimethylbenzamide with methylamine in some catalytic condition would give N-methylbenzamide.
Convert of dimethylaniline to methylaniline is also reported by using TBHP-CuCl condition. The mechanism is oxidation of one methyl to CH2+ and removed.
Dr. Nizar,
It is possible depending on R group of CO-NRR', e.g.
For N-allyl-N-methyl the deallylation by Pd II complexes is reported. see
--- Ohmura, Naoya et al, European Journal of Organic Chemistry, (30), 5042-5045, S5042/1-S5042/5; 2008.
For N-benzyl-N-methyl the debenzylation by by N-bromosuccinimide is reported. see
---Kuang, Liping et al, Synthesis, (20), 3129-3134; 2007.
Good luck
Thanks a lot Dr. Adel. You are very kind. I really want to see if there is work on two similar groups attached to N (2 methyls or 2 ethyls) & this work includes taking one & leaving one. If there is such work, then it will open up an excellent path for research in (polymer chemistry) .
Thanks a lot Dr. Yan. I need references to see what the researches have done in some detail.
For transamidation, see: http://pubs.acs.org/doi/abs/10.1021/ol301308c
http://pubs.acs.org/doi/abs/10.1021/jo500562w
For oxidative demethylation, see:
http://www.organic-chemistry.org/abstracts/literature/499.shtm
http://www.ncbi.nlm.nih.gov/pubmed/2500128
Liao Q, Xi C-J. CuCl-catalyzed oxidative N-demethylation of arylamines with t-butyl hydroperoxide. Chem. Res. Chin. Univ. 2009, 25: 861-865.
You can also use the keyword demethylation dimethylaniline in google search, and you can get a lot of result.
Thanks Dr. Yan, I saw the 4 references but they did not give answer to the question attached below. I want to remove one methyl & keep the other methyl.
It is alright if I find a way to convert N,N-diethylbenzamide into N-ethylbenzamide
(also removing an ethyl & keeping the other ethyl).
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