I purchased 3 new songs that will not download to my ipod nano 1st generation

can someone help me with downloading songs that will not transfer from itunes to my ipod nano 1st generation that already has songs downloaded?

HI robamish,
The only idea I have is you can restore your ipod nano to your factory settings and that could work. If you don,t know how to restore your ipod nano or if you have any question please reply back!!!!

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