Efficient Consecutive Synthesis of Ethyl-2-(4-Aminophenoxy) Acetate, a Precursor for Dual GK and PPARγ Activators, X-ray Structure, Hirshfeld Analysis, and DFT Studies

Herein, we report a facile synthesis of ethyl-2-(4-aminophenoxy)acetate 4 as building synthon for novel dual hypoglycemic agents. This template was synthesized by alkylation 4-nitrophenol with ethyl bromo-acetate followed selective reduction the nitro group. methoddoes not require nascent hydrogen or any reaction complexity; it goes easily via consecutive in NH4Cl/Fe to yield our target very pure crystals. product characterized 1HNMR, 13CNMR, COSY, NOESY NMR spectroscopy, and elemental analysis. Additionally, its structure studied approved X-ray single crystal determination. The unit cell parameters are = 8.2104(6)Å, b 10.3625(9)Å, c 11.9562(9)Å, α 101.787(7), β 91.849(6), γ 102.755(7)°, indicating that crystallized triclinic system. cooperative non-covalent interactions also discussed aid Hirshfeld surface H…H, H…C, O…H have major contribution molecular packing 4. Moreover, different quantum chemical were computed based on DFT calculations. experimental UV/Vis spectra showed two bands at 299 234 nm, which calculated using TD-DFT method 286 (f 0.068) 226 nm 0.294), respectively. These assigned HOMO→LUMO (95%) HOMO→LUMO+2 (86%) transitions,