Question about N-dealkylation

[Harald Deinhammer]

Hello,

I惴 looking for a possibility to dealkylate N,N-dimethyl-p-toluidine to receive
N-methyl-p-toluidine. CA and Beilstein search revealed only a possibility which
involves Cytochromoxidase (never worked with Enzymes before), and an alternate
which works by leading a stream of a certain gas (HBr i guess?) through the molten
substance (yielding only 30% of my desired product).

If you know a better way to perform the dealkylation i would be very pleased to
hear from you.(Please include the citation where it was published)

Thanks in advance,
Harald Deinhammer

PS.: Please reply by E-mail, since i am not consequently reading this newsgroup

--
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Harald Deinhammer alias har...@sbox.tu-graz.ac.at

There愀 no vestige of a beginning, no prospect of an end.
When we all dsintegrate it will all happen again, yeah.
Bad Religion, No Control

[Ulrich Heigl]

The best non enzymatic method should be the one from

Volz et al. Justus Liebigs Ann. Chem. 7752,86(1991) with a yield of 93%.
The methylenimminium perchlorate formed is hydrolyzed with water.

For another method see:

Acosta et al. J. Chem. Soc. Chem. Commun. 1994,(17)p1985,1994.

I hope this helps.

[Ulrich Heigl]

[Ulrich Heigl]

Best method to your problem:

Volz et al. Justus Liebigs Ann. Chem. 752,86(1971)

The methylimminium perchlorate is hydrolized with water. Yield 93%

see also:

Acosta et al. J. Chem. Soc. Chem. Commun. 1994,(17), p.1995,1994.

I hope this helps