Direct C-H functionalization of aromatic compounds is a powerful tool for organic synthesis; however, differentiation among the ubiquitous and often chemically similar C-H bonds remains a significant challenge. Conflation with coordinating or directing groups incorporated into the intended substrate has helped address these limitations, although access to remote sites remains limited. Herein, we report an operationally simple and sustainable direct meta-selective H2N amination of benzylic and related aromatic picolinates under conditions mild enough to modify polyfunctional and late-stage molecules.