Using mild conditions, the aminoquinoline directing group could be removed in a divergent manner. The N-Boc protected aminoquinoline amide intermediate was used to unveil alcohol, carboxylic acid, amide and nitriles functionalities. The obtained products afforded fragments with desirable physicochemical properties for fragment-based drug discovery. Valuable fragments of this defined substitution pattern featuring a polar ring heteroatom, a C(4) polar functional group, and a C(3) aryl group were accessed in only 3-4 high-yielding steps from inexpensive commercial materials.