Water → HCID 22148907, compound

Participants

Reaction Steps

To a solution of nitrobenzene 51 (2.07 g) and NH4Cl (1.84 g) in EtOH (40 mL) —H2O (10 mL), was added iron powder (1.92 g). The mixture was heated to reflux for 1 h. After cooling the reaction mixture was filtered through short celite pad. The filtrate was concentrated, diluted with sat. NaHCO3 (30 mL) and extracted with AcOEt (30 mL). The combined organic layers were washed with brine (30 mL) and dried over Na2SO4. Concentration of the solvent afforded the aniline 52 (1.77 g, 95%) as a yellow solid. 1H NMR (300 MHz/CDCl3) δ 3.77 (2H, brs), 6.63 (1H, dd, J=2.7 Hz, J=8.6 Hz), 6.83 (1H, d, J=2.7 Hz), 6.99 (1H, d, J=8.6 Hz), 7.24 (1H, d, J=2.8 Hz), 7.49 (1H, m), 7.56-7.64 (2H, m), 8.08 (1H, m), 8.86 (1H, J=2.8 Hz)

Provenance & Evidence