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Topic: Oxim synthesis  (Read 3225 times)

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ptb969

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Oxim synthesis
« on: April 04, 2008, 08:32:16 AM »
Hallo,
today I have read an article describing a way to synthesize oxim from methyl acetoacetate using NaNO2 in acetic acid (See the scheme attached here). I do not really figure out the mechanism of this reaction.

Could any one give a suggestion.
As far as I know, to prepare an oxim, people start from a carbonyl compound reacting with hydroxyl amine.
Best regards,
CPC
« Last Edit: April 21, 2008, 04:59:37 PM by CPC »
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Offline Dan

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Re: Oxim synthesis
« Reply #1 on: April 04, 2008, 08:55:44 AM »
NaNO2 in acid can generate NO+, so I expect that's your electrophile. The enol from MAA will be your nucleophile.
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ptb969

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Re: Oxim synthesis
« Reply #2 on: April 04, 2008, 09:08:44 AM »
Oh, Dan,
thank you very much for a quick suggestion. I appreciate that very much.
You know I have prepared oxim only once so I am not quite experienced with that.

Sincerely,
CPC
« Last Edit: April 21, 2008, 05:00:03 PM by CPC »
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