Hydrochloric Acid → HCID 22136223, compound

Participants

Reaction Steps

To a solution of 2-nitro-6-(phenoxy)benzonitrile (Example 113c) (1.94 g, 8.08 mmol) in MeOH (164 mL) was slowly added concentrated HCl (7.23 mL) followed by iron powder (1.58 g, 28.3 mmol). The reaction was refluxed for 30 min and concentrated in vacuo. The residue was dissolved in EtOAc and washed with 1N NaOH, water and brine. The organic layer was dried over MgSO4, filtered, concentrated and purified by flash chromatography 1:1 Hexane:EtOAc to yield 2-amino-6-phenoxybenzonitrile (384 mg, 22.6%). 1H NMR (400 MHz, MeOD) δ 5.97 (d, J=8.3 Hz, 1H), 6.50 (d, J=8.6 Hz, 1H), 7.06 (m, 2H), 7.18 (m, 2H), 7.40 (m, 2H). MS 210 (MH+).

Provenance & Evidence