A selective ortho-olefination of primary amides yields valuable motifs for pharmaceuticals. Primary amide-directed ortho-olefination of benzamide using unactivated alkenes was successfully conducted with a ruthenium(II) catalyst. The established protocol demonstrates efficacy across various benzamides, achieving moderate to good yields with high functional group tolerance. Furthermore, the transformation of ortho-olefinated amides into five-membered lactams highlights their synthetic applicability in the pharmaceutical sector.