3-(1,3-OXAZOL-5-YL)ANILINE

89808-77-5

157837-31-5

General procedure for the synthesis of 3-(5-oxazolyl)aniline using 5-(3-nitrophenyl)oxazole as starting material: firstly, intermediate 1a (3.52 g, 18.5 mmol) was dissolved in anhydrous ethanol (210 ml), followed by addition of water (21 ml) for dilution. Next, SnCl2-2H2O (20.9 g, 92.6 mmol) and HCl (15 ml, 180 mmol) were added to the reaction system. After the reaction mixture was stirred overnight at room temperature, the pH was adjusted using 10% NaOH aqueous solution to 7. Subsequently, the reaction mixture was extracted several times with EtOAc. The organic phases were combined, dried with MgSO4, filtered and the solvent was evaporated to give 3-(5-oxazolyl)aniline in the form of a light orange powder (2.74 g, 93% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) with chemical shifts of δ8.37 (s, 1H), 7.49 (s, 1H), 7.10 (t, J=7.8 Hz, 1H), 6.90 (t, J=1.8 Hz, 1H), 6.86 (d, J=7.6 Hz, 1H), 6.59-6.54 ( m, 1H), 5.25 (s, 2H).