DOC

[Natrix]

D. Ehlers, J. Schäning - Synthese von DOC (2,5-Dimethoxy-4-chloramphetamin):

http://www.gtfch.org/tk/tk68_2/Ehlers.pdf

[PrimoPyro]

I assume the reaction of the amine with acetic anhydride, forming the acetamide, is done as an amine protecting function for the aromatic nitration step?

Is this the reasoning behind this step?

                                                 PrimoPyro
Vivent Longtemps la Ruche! STRIKE For President!

[Rhodium]

Yes, it is a protection group. It also protects the nitrogen from being oxidized by the nitrous acid in the diazotization step. Good find, Natrix!

[Aurelius]

Rhodium, could you add that to your page (in english?)

[Rhodium]

Yes, I'll translate it when I have the time.

[Osmium]

Well, it's interesting but not very much suited as a production guide. An 8 step synth with sometimes dramatically shitty yields.
But it is the first chemistry ref. I have seen which cited Pihkal!  

[yellium]

It's a shitty synth, but direct chlorination isn't perfect either. The issues with di/trichlorination are for real. And using NCS isn't that much of an improvement if you want to obtain reasonably pure 2C-C/DOC.

[Rhodium]

I believe the protection/deprotecting scheme can be omitted, if the product is carefully puified afterwards, and that a low enough pH is used in the diazotizing step to minimize any reaction of the aliphatic amine with the nitrous acid (aliphatic amines are less reactive at low pH's, but not aromatic amines).

[moo]

If it is so, that even a LAH reduction can be done without damaging the aromatic halogen, then what is wrong with adding the halogen to the benzaldehyde and then proceeding as one wishes. For example, the use of Ca(OCl)₂ will only monochlorinate. I would like to know, because it seems there is some reason behind all this I haven't been able to find out. Oh, and there are countries where 2,5-DMA is illegal but DOC is not.
^{understanding is everything}

[Rhodium]

LAH would probably rip off the chlorine substituent if it was present on the nitrostyrene. Either another reducing agent like AlH3 should be used, or the chlorine has to be put there afterwards.

The document is now translated and placed on my page:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/doc.synth.html

(please point out any errors that I may have made)