If your legacy system can use a proxy server, as Dove suggests, you can use something like Foxy to do the redirection. I'm not sure, but I believe that some software uses IE to transport HTTP, so try installing the HTTP proxy in IE on the client machine?
If this is not the case, I think this is a difficult problem, since in essence you are trying to intercept and modify TCP / IP traffic, which, in my opinion, is possible only with the help of an advanced firewall or router.
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