[hpl912]

how does PCl5 reacts in this reaction?
should it chlorinate or remove the proton from the OH?
i see there is a benzene ring shift (sigmatropic rearrangement?) from C to N... or should the OH that is initially attached to N completely leave, benzene shift and then the -OH of the H2O attaches to the C and then rearranging in a O double bond?



thanks for any suggestion/help

[lancenti]

I don't see how a chlorination will help, so I'm guessing it can remove the  OH thus forming C=N⁺ from which I can shift my benzene ring over and form my carbocation to be attacked by water, then proton shift to change the C=N-Ar into a C-NH-Ar, then lose the last proton on the new C-O-H to get my C=O.