3-Aminophenol → 4-(3-Aminophenoxy)-3-nitropyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

3-Hydroxyaniline (2.07 g, 19.0 mmol) was dissolved in dry DMF (65 mL) and the solution was degassed by argon bubbling for 10 minutes. Potassium tert-butoxide (2.13 g, 19.0 mmol) was added and the stirring was continued for 1 hour at room temperature. 4-Chloro-3-nitropyridin-2-amine (3.0 g, 17.3 mmol) was added as a solid in one portion and the reaction mixture was subsequently heated at 80° C. for 20 hours. The solvent was evaporated in vacuo and the brown oily residue was taken up in 1M HCl (aq) (50 mL). This layer was washed with EtOAc (3×50 mL) and subsequently basified to pH ˜10 with 1M NaOH (aq). The brown precipitate was collected, washed with H2O (3×25 mL) and dried in vacuo, to afford 4-(3-aminophenoxy)-3-nitropyridin-2-amine (3.50 g, 80%). 1H-NMR (δ, ppm, DMSO-d6): 5.39 (s, 2H, NH2), 6.02 (d, 1H, HPy,5, J=5.7 Hz), 6.23-6.30 (m, 2H, Harom,Ph′), 6.47 (d, 1H, Harom,Ph′, J=8.0 Hz), 7.04-7.24 (m, 3H, NH2+Harom,Ph′), 7.48 (m, 2H, Harom), 7.98 (d, 1H, HPy,5); LC-MS (m/z): 247 (M+H, 100).

Provenance & Evidence