Benzaldehydes from diazonium salt, OTC!

[Tricky]

Look at this!



it's from

http://www.orgsyn.org/orgsyn/prep.asp?rxntypeid=80&prep=CV5P0139

If one use 4-methyl-2,5-dimethoxyanilin (wich easy to produce by reduction of 4-nitro-2,5-benzaldehyde, wich produced by nitration of 2,5-DMBA) instead of 4-methyl-2-bromoanilin, finaly we produce 4-methyl-2,5-DMBA a direct precursor for DOM  
SWIT also thinks it's easy way to some other pretty X-methyl-phenethylamines.
Matrix... may tricks?

[kurupira]

Questions to experienced bees:
Is this reaction useful to methoxy (or methylenedioxy) aninlines?

if so:   
if not:  

[kurupira]

Sorry,   i was thinking using this reaction after a Schmidt rearrangement (Vogel p898-9), that would bee an interesting route to piperonal from piperonylic acid (obtained from piperine), but i don't think the methylenedioxy ring will survive the Schmidt reaction (10% oleum/sulfuric acid medium)... anyway it could bee aplied to other benzoic acids.