4-Methoxy-2-nitrobenzonitrile → 4-Hydroxy-2-nitrobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxy-2-nitrobenzonitrile (820 mg, 4.6 mmol) and pyridine hydrochloride (755 mg, 4.6 mmol) was heated at 200° C. under N2 for 18 hours. Upon completion, the reaction was cooled to room temperature, washed with brine and extracted with EtOAc (2×100 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (1:1 Hexane:EtOAc) to provide 4-hydroxy-2-nitrobenzonitrile (200 mg, 26%). 1H NMR (400 MHz, MeOD) δ 7.24 (dd, J=8.6, 2.4 Hz, 1H), 7.70 (d, J=2.4 Hz, 1H), 7.83 (d, J=8.6 Hz, 1H).

Provenance & Evidence