Hydrochloric Acid → HCID 14499221, compound

Participants

Reaction Steps

To a solution of 190 mg (0.72 mmol) of 4-[(6-methoxy-2-naphthyl)amino]phenol (prepared as described in Example 2) and 0.50 ml of pyridine (dried over KOH) in 4 ml of dry CH2Cl2 at 0° was added dropwise over 5 minutes 55 ul (0.77 mmol) of acetyl chloride. The reaction mixture was stirred for 30 minutes then added to 25 ml of 1N aqueous HCl solution and extracted with 25 ml of warm ethyl acetate. The organic extract was washed with an additional 25 ml of 1M aqueous HCl solution, dried (MgSO4) and concentrated in vacuo to give a solid. The crude solid was purified by flash chromatography (silica gel, 10×3.0 cm, 1:1 EtOAc/petroleum ether) followed by recrystallization (EtOAc/petroleum ether) to afford 145 mg (66%) of title compound as white crystals, m.p. 187°-188°.

Provenance & Evidence