Acetyl chloride → N-(2,6-dihydroxyphenyl)acetamide

Participants

Reaction Steps

A mixture of 2-nitroresorcinol (1.0 g, 6.45 mmol) and 10% Pd—C (100 mg) in methanol (15 mL) was stirred under an atmosphere of hydrogen at ambient temperature for 4 hours. The reaction mixture was filtered through celite and the filtrate concentrated under reduced pressure. A mixture of the residue, triethylamine (1.8 mL, 12.9 mmol) and acetyl chloride (1.38 mL, 19.35 mmol) in dichloromethane (15 mL) was stirred at ambient temperature for 1 hour, poured into 1N NaOH (20 mL) and methanol (20 mL). After 10 minutes, the mixture was concentrated under reduced pressure and taken up in ethyl acetate and 1N HCl (50 mL, 1:1). The layers were separated and the organic phase was washed with brine, dried (MgSO4), filtered and concentrated to provide titled compound. MS (ESI (−)) m/e 166(M−H)+; 1H NMR (300 MHz, DMSO-d6) 9.31(s, 2H), 6.86 (t, 1H), 6.34 (d, 2H), 2.11(s, 3H).

Provenance & Evidence