[sj3107]

I am trying to workout the mechanism to produce the circled compound. The diketone on the right is necessary but I am unsure about the nucleophile that I have proposed. I have drawn what I think it may be in red underneath the compound that I am trying to synthesise. Would anyone be able to help check my chemistry - am I using the correct nucleophile?

[rolnor]

I am worried that the p-nitro group makes the aniline a very weak nuchleophile, that could be a problem. Maybe it can be solved by heating the reaction mixture?

[sj3107]

I am worried that the p-nitro group makes the aniline a very weak nuchleophile, that could be a problem. Maybe it can be solved by heating the reaction mixture?

Yes good idea, do you think it is the correct nucleophile for the reaction other than potential reaction barriers?

[rolnor]

I would think so, have you made a litterature search? The product would be sensitive to oxidation, or what do you think? It want to aromatizise?

[wildfyr]

Rolnor, I think this is "on paper" chemistry, and the precise reactivity of the aniline is not an issue.

Now if its in a flask... I'm with you, some extra trickery could be involved. Or as my highly experienced synthesis coworker once said  "sometimes you just have to f&#^$*@ heat the f&#^$*@ s#*$ out of it."

[rolnor]

Rolnor, I think this is "on paper" chemistry, and the precise reactivity of the aniline is not an issue.

Now if its in a flask... I'm with you, some extra trickery could be involved. Or as my highly experienced synthesis coworker once said  "sometimes you just have to f&#^$*@ heat the f&#^$*@ s#*$ out of it."

OK, I see. I think one should take only use published chemistry for this type of exersise othervise the student dont learn correctly?