Van has an old iPod Nano and wants to back up the media from it. iTunes doesn't work because while it sees the Nano, it's grayed out. So you can't really do anything with it. Leo recommends iMazing. It will work with any "i device." They have a free trial before you buy it. Another option is the Wondershare Doctor Phone. It specifically says it supports the iPod Nano. You can also try eCamm PhoneView.