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ethylamine synthesis from acetylene 13 years 6 months ago #766

Hello,

what a problem, how do I synthesize ethylamine starting from acetylene as the only carbon source, try to convert it to ethanal and then to amide for its reduction and get the amine, but I have propylamine left...???

What can you advise me?

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Re: ethylamine synthesis from acetylene 13 years 6 months ago #767

Man, it seems clear that there is no interest in a carbonyl group from what you say, then you can't load it, just add + carbons and that doesn't matter.

A simple idea, perhaps would be the reduction of acetylene to ethylene with H2/Lindlar's catalyst, then brominate the alkene with HBr and finally add NH3 (SN2 nucleophilic substitution).

Let's see if it works for you

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Re: ethylamine synthesis from acetylene 13 years 6 months ago #769

Thank you, I did not take this reaction into account due to chemoselectivity, in this I do not have such a high efficiency due to the competition of ammonia or the primary amine, to continue substituting secondary and tertiary amines.

I see the reductive amination of ethanal as very possible.

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Re: ethylamine synthesis from acetylene 13 years 6 months ago #771

Reductive amination is the proper method to obtain amines from aldehydes and ketones.

The reaction between haloalkanes and ammonia is not a good method, it produces a mixture of primary, secondary, tertiary amines and ammonium salts.

Greetings to all

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Re: ethylamine synthesis from acetylene 13 years 6 months ago #774

You can do the reaction that oxk told you but instead of ammonia use sodium azide and then reduce it!
obtaining the primary amine Greetings,
I just flew, I was in some trouble...:P

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Re: ethylamine synthesis from acetylene 13 years 6 months ago #799

Following the initial reasoning of acontreras, you arrived at acetamide which, by conventional reduction, becomes propylamine.
I have been reviewing the subject of amines, with which I have come across Hoffmann's reaction that seems to be perfect; Treating the acetamide with Br2 in a basic aqueous medium, ethylamine + CO2 would be formed, so we can remove the carbonyl group. The mechanism of the reaction is complex.

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