OrthancsChemist
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looking for path from Acetic acid to Gylcine
Howdy, Im looking for a way to add NH2 to a terminal alkane or the CH3 part of the acetic acid at least. I suspect I will need
to use a protecting group for the carboxylic acid, but I'm not familiar with an NH2 additions.
Any known reactions that add NH2 would be appreciated
I'm taking the solvents to Isengard
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Texium
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Unfortunately you can’t just stick an NH2 group onto an alkyl chain.
The most direct way would probably be 2 steps via Hell-Volhard-Zelinsky to make bromoacetic acid followed by ammonolysis to yield glycine. It’s not
practical though, and requires phosphorus tribromide. You’d be much better off buying glycine. It’s widely available as a supplement.
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Texium
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Thread Moved
14-3-2025 at 16:20 |
OrthancsChemist
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Apologies for posting in the wrong space.
I figured it wasn't practical nor economical. I noticed how close Glycine was to acetic acid so I was curious to see if there was a pathway.
I'm taking the solvents to Isengard
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Keras
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From succinic acid though, you could (in theory?) obtain a mono amide and then use a Hoffmann rearrangement to get glycine.
OH-CO-CH₂-CO-OH → OH-CO-CH₂-CO-NH₂ → OH-CO-CH₂-NH₂
Can’t you obtain succinic acid by oxidising butanoic acid with potassium permanganate?
In any case, it’s not starting from acetic acid…
[Edited on 15-3-2025 by Keras]
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phlogiston
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Small remark: the trivial name for the 3-carbon dicarboxyic acid is malonic acid (not succinic acid).
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