dormouse (Member)
04-21-00 03:05
No 108431
      Thoughts on 3,4-methylenedioxy aniline...? -Snidely Whiplash  Bookmark   


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Author  Topic:   Thoughts on 3,4-methylenedioxy aniline...? 
Snidely Whiplash
Member   posted 07-15-98 11:55 PM          
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I'm curious to hear if anyone has any thoughts regarding interesting uses for
3,4-(methylenedioxy)aliline, cas 14268-66-7.
 
Rhodium
Administrator   posted 07-16-98 09:08 AM          
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Diazotization to bromo-benzodioxole, followed by methanolysis with CuBr/NaOMe/EtOAc to form a MMDA precursor after vilsmeier formylation?
 
drone 342
Member   posted 07-16-98 04:03 PM          
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Alternatively, after forming bromobenzodioxole, reaction with the enolate of acetone to make MDP-2-P (Gawd, I love enolates!)
-drone #342


assholium
Member   posted 07-18-98 12:17 PM          
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>Diazotization to bromo-benzodioxole
Rhodium, there is more elegant ways: f.e. Meerwein rxn(MD-diasonium with methacrylamide -> 2-(1,3-benzodioxol-5-yl)propanoic acid amide ~45-50%), and the Hofman degradation of resulting amide to MDA (70%). 2 steps; overall conversion I guess near 30%...


Snidely Whiplash
Member   posted 07-18-98 07:34 PM          
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So I guess my next question is: Would
3,4-methylenedioxy aniline be a better starting point than other, more conventional, chemicals?
Thanks!


Lone Ranger
unregistered   posted 07-20-98 06:07 PM           
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Far better starting points would be the acetic acid, or the aldehyde. Less steps are then needed. What is the BEST starting point?? This is relative, it depends on what you can get, and what reagants are available to you. Price is also a factor. I have found that the substituted aldehydes are available, and cheap.
 
rubberneck
unregistered   posted 07-23-98 04:01 AM           
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Lone Ranger, you say that substituted aldehydes are available and cheap? is pipernal the substituted aldehyde of which you speak? Tell us of sources, yes please tell.
 
Lone Ranger
unregistered   posted 07-24-98 02:19 PM           
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Fischer.
 
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