Furboffle
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Primary amine oxidation
I'm trying to figure a good way to get from a primary amine to a carboxylic acid.
I used the search engine but only found possible means of converting to a primary alcohol, but I want this to be broader.
Whether converting the NH2 to A primary alcohol or a carboxylic acid or an amide. Cnversion to a carboxylic acid would be ideal, to amide would be
nice, then hydrolysis of the amide would be simple, but if nothing else primary alcohol will do then use an oxidizing agent. Would reacting with a
strong acid work to protonate to ammonium and act as a leaving group to substitute an -OH? Or would the ammonium salt be too stable to proceed with
removing ammonia?
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Prometheus23
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Primary amines can be dichlorinated with TCCA in dichloromethane and then reacted with a base such as triethylamine to yield a nitrile. This nitrile
can then be hydrolyzed with sulfuric acid in water to give the carboxylic acid. I don't have the reference in front of me, but if you search for
"amine" "tcca" "chloramines" etc in google I'm sure you will find it easily.
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Nicodem
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Thread Moved
2-11-2012 at 04:21 |
Nicodem
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Your question is too vague for an answer. It is not even clear if you want a homologated carboxylic derivative or transform a -CH2NH2 group into
-COOH. You also do not provide enough details about the substrate, so any answer would be mere guesswork.
If you UTFSE, you can see that the topic of transforming the amino group into a leaving group was already discussed. In some specific cases you can transform the amino group into a leaving group by peralkylation. But a protonated amino group only works as a leaving group when the nucleophile is near neutral.
PS: Please open new threads without references only in the Beginnings section. See the forum guidelines for more info.
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scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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