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I'm a big believer in time out, but if it isn't working maybe it is time to switch to something else. How about immediate loss of a favorite toy? Hit=favorite toy goes on a top shelf with no discussion, just a simple "no hitting. you may have this toy back tomorrow." Then if he throws a fit, that gets a removal to his room with "you need to have your own space until you are calm" and no mention of the hitting. Then every morning take a minute to give back the toys he lost. Ask him why he lost the toys and what he can do today to keep it from happening again. Brainstorm some other things he can do if he is frustrated about not getting what he wants, but keep the whole toy giving back and conversation less than three minutes long to keep his attention focused.

Have you tried the books? Hands are not for hitting, etc...

Ugh hitting is so rough. It brings out so many strong emotions in the adult, as well as the kid! I work in early childhood and see a lot of kids who are aggressive. In my experience, kids don't really want to hurt anyone, they are just out of control & feeling a lot of pent up emotion. Here's what has worked for me most of the time:
1) be hyper-vigilant of situations that may upset your son. Look for patterns and try to be there to stop the hit before it happens. (I gently catch hands or bear-hug when I see a hit coming) This is really key, it's easier to deal with the anger if there was no hitting. If your too late, keep calm & have your son sit close, but address the person who was hit first.
2) no time-outs, even if the hit landed. Talking right away creates a better connection for what to do instead. So, I say something like "I can tell your very mad about X, but I won't let you hit/hitting is hurtful." I try to talk to them about whatever happened, help them calm down (sometimes they are raging and I have them sit in a spot close to me until they are calm), and help them think of a solution to whatever is happening.
3) Connect more during the day. I try to spend lots of time doing positive things with the kids who are aggressive in my class.

Habitual hitting usually stems more from unresolved fears (maybe he is concerned deep down about the new baby?) and isn't so much about the immediate anger of a situation.

@creativemomma15: I'm glad that seemed helpful! I hear you on trying to stay calm. We had a rough night/tantrumy wake-up and I had to send my son to his room to scream while I hid in my closet to calm down. It's so hard to be cool and collected, especially when the kids act so irrationally.