With the head rotated through 90 degrees, can you actually get the axis of the cutter close enough to the table?
Chronos I think, and maybe others, do a right angle adaptor that fits certain mills with quills of particular diameter.
However I question the need in most cases. You take the same cutter and fit it conventionally and then cut along the side of the job – that will produce a keyway with a curved runout, rather than one with a radiused end, if that’s what is needed. I’d hold that in a dividing head and tailstock for convenience.
I you want to start milling crankshafts and journals, that’s a slightly different matter, and going truly horizontal is more important, but for the odd keyway etc, is it worth disturbing a carefully set up head when it isn’t essential?