4-Aminophenol → 4-(2-Chloro-pyridin-4-yloxy)-phenylamine

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Reaction Steps

4-amino-phenol (8.9 g, 81.6 mmol) and potassium tert-butoxide (10.7 g, 95.2 mmol) were suspended in DMF (100 mL) and stirred at RT for 30 min. 2,4-Dichloro-pyridine (10 g, 68 mmol) was added and the resulting mixture was heated to 90° C. for 3 h. The solvent was removed under vacuum and the residue was extracted with DCM (2×100 mL). The combined organics were dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to afford 4-(2-chloro-pyridin-4-yloxy)-phenylamine (9.0 g, 60% yield). 1H NMR (DMSO-d6): δ 8.21 (d, J=5.6 Hz, 1 H), 6.85-6.82 (m, 4 H), 6.61 (d, J=6.6 Hz, 2 H), 5.17 (s, 2 H); MS (ESI) m/z: 221 (M+H+).

Provenance & Evidence