how to upload music to vintage iPod mp3 player

Instead of looking at the Device/Music option (as shown in your screenshot), click on the iPod icon at the top of the iTunes window:

That will display the Device/Settings/Summary pane. (My screenshots show iTunes for Windows, but for this purpose they are the same thing and will help solve this issue for you.)

Once the Summary pane is showing:

• • click on the Device/Settings/Music option (1. in the screenshot below):

• • tap the Sync Music option (2.) so that there is a tick (checkmark) in the box
  • in this next step (3.), choose either:
    • Entire music library (3.), which will try to add all the music in your iTunes library to the iPod. (Note that sections numbered 4. will not be displayed.) However, your iPod looks to me like either a first generation iPod nano (in which case, it has either 1GB, 2GB, or 4GB of storage, or a second gen iPod nano, in which case it will have either 2GB, 4GB or 8GB of storage, neither of which is very much). If your Library has more music in it than your iPod can store, you will see a message telling you that "extra space is required" (odd message since you can't add more storage, but that's Apple for you). If this happens, use the next option
    • Selected playlists, albums, artists and genres (3.), which will then display sections numbered 4. You can then select which items you want to be added to your iPod from the various sections (Playlists, Artists, Albums and Genres). This will allow you to limit what is added to the iPod. If you need to use this method, there is a neat trick that makes this easier to manage, please ask about it if you're interested
  • tap the Sync (or Apply) button in the lower right corner of your iTunes window (not shown in the screenshots) for these settings to take effect

That's it, your iPod is set up to use and should now have music from your library on it. If you use the sync selected playlists... option, it's possible to set up a Smart Playlist or two that will automatically add and remove music from the iPod at each Sync. As mentioned above, if you're interested, please ask for more information.

first of all, backup your music library and store it in safe place

put it into disk mode > then press on shift + cmd + period ( . ) > iPod Control > Music

There will be bunch of F folders, back them up

after that sync your ipod with your main machine, then you can put music on it, head up to spotify - downloader com, there you can get your music, that is the "easy" way to get your music though, using that site myself :P

Then drag n drop your downloaded music to your library

i hope u get me :D