4-methoxy-N-(4-nitrophenyl)aniline → HCID 10243439, compound

Participants

Reaction Conditions

Reaction Steps

To 4-methoxy-N-(4-nitrophenyl)aniline (785 mg, 3.2 mmol) in 5 mL of AcOH was added Pd(OAc)2 (1.43 g, 6.4 mmol). The mixture was heated at 100° C. for 15 h under air atmosphere and cooled to rt and concentrated under reduced pressure. The residue was taken up in EtOAc (100 mL) and washed with NaHCO3 (2×100 mL) and water (100 mL). After solvent removal, the crude was purified with chromatography (hexane/EtOAc) to afford 3-methoxy-6-nitro-9H-carbazole as a orange solid (495 mg, 64%). 1H NMR (400 MHz, acetone-d6) δ 10.90 (s, 1H), 9.09 (d, J=2.4 Hz, 1H), 8.27 (dd, J=9.2, 2.4 Hz, 1H), 7.96 (d, J=2.4 Hz, 1H), 7.62 (d, J=9.2 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.14 (dd, J=8.8, 2.8 Hz, 1H), 3.92 (s, 3H); MS (ESI) m/z 243 (M+H+).

Provenance & Evidence