Methanol → 4-(4-chloro-1H-imidazol-1-yl)-3-allyloxyaniline

Participants

Reaction Conditions

Reaction Steps

Iron powder-325 mesh (737 mg, 12.5 mmol) was added to a round bottom flask charged with a mixture of 1-(2-(allyloxy)-4-nitrophenyl)-4-chloro-1H-imidazole (500 mg, 1.8 mmol), absolute methanol (10 mL), and ammonium chloride (768 mg, 14 mmol). A water-cooled reflux condenser was attached to the flask and the heterogeneous mixture was heated to 65° C. with vigorous stirring for 30 min. The reaction mixture was filtered, and washed with methanol. The solvent was removed in vacuo. EtOAc was added to the residue, and washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 4-(4-chloro-1H-imidazol-1-yl)-3-allyloxyaniline (380 mg, 83% yield). LC-MS (M+H)+250.0. 1H NMR (500 MHz, CDCl3) δ ppm 7.48 (d, J=1.22 Hz, 1H), 6.97-7.02 (m, 2H), 6.26-6.32 (m, 2H), 5.87-5.98 (m, 1H), 5.20-5.34 (m, 2H), 4.48 (d, J=5.19 Hz, 2H), 3.86 (br s, 2H).

Provenance & Evidence