Water → 2-Azidoaniline

Participants

Reaction Steps

To a suspension of the of 2-(2-azido-phenyl)-isoindole-1,3-dione (373 mg, 1.4 mmol) in ethanol (10 mL) was added hydrazine (140 μL, 4.24 mmol) followed by stirring for 15 minutes. The reaction mixture was poured into water and was extracted with ethyl acetate (3×25 mL). The combined extracts were washed with water and brine and were dried over magnesium sulfate. Filtration and concentration in vacuo gave a residue which was purified via radial chromatography (1 mm plate, 10% ethyl acetate/hexanes to 33% ethyl acetate/hexanes gradient elution) to give 48 mg (25%) of 2-azidophenylamine as a solid: 1H NMR (300 MHz, DMSO-d6) δ 6.98 (m, 1H), 6.86 (m, 1H), 6.66–6.55 (m, 2H).

Provenance & Evidence