Hydrochloric Acid → 3-Amino-4-hydroxybenzonitrile

Participants

Reaction Steps

To a mixture of 5 g (30.5 mmol) of 4-hydroxy-3-nitrobenzonitrile, 18.1 g of powder tin metal (152.5 mmol, 325 mesh), and 45 mL of ethanol was added with stirring a solution of 10 mL of concentrated HCl in 30 mL of H2O. The suspension was heated at reflux for 45 min and the resulting hot solution was poured into 100 mL of H2O. Saturated aqueous NaHCO3 solution was slowly added to bring the pH to ca. 7. The suspension was filtered, and the residue was washed with MeOH giving the title compound (3.15 g, 77%) as a white powder. Rf (CH2Cl2/MeOH 9:1) 0.47; 1H NMR (CD3OD) δ 6.96 (d, 1H, J=1.3 Hz, H-2), 6.92 (d, 1H, J=8.1 Hz, H-6), 6.75 (d, 1H, J=8.1 Hz, H-5); 13C NMR (CD3OD) δ 151.1 (C-4), 138.6 (C-3), 124.7 (C-6), 121.6 (CN), 119.1 (C-2), 115.9 (C-5), 103.6 (C-1).

Provenance & Evidence