4-Amino-3-hydroxy-benzonitrile

18495-15-3

55586-26-0

The general procedure for the synthesis of 4-amino-3-hydroxybenzonitrile from 3-hydroxy-4-nitrobenzonitrile was as follows: 3-hydroxy-4-nitrobenzonitrile (1.6 g, 9.6 mmol) was dissolved in a solvent mixture of ethanol (40 mL) and N,N-dimethylformamide (20 mL). Palladium hydroxide (30 mg) was added to this solution to form a reaction mixture. The reaction mixture was stirred overnight at room temperature in a hydrogen atmosphere. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst and the solvent was subsequently removed by distillation under reduced pressure. The residue was dried to afford crystals of 4-amino-3-hydroxybenzonitrile (771 mg, 60% yield). The product was characterized by 1H-NMR (DMSO-d6) with the following chemical shifts: δ 5.57 (2H, broad peak), 6.62 (1H, double peak, J = 8.4 Hz), 6.86 (1H, double peak, J = 2.2 Hz), and 6.99 (1H, double-double peak, J = 1.9 Hz, 8.1 Hz).