Water → Methyl 2-(acetylamino)benzoate

Participants

Reaction Steps

A solution consisting of 20 mL of acetic anhydride in 100 mL of methylene chloride was stirred at room temperature and 20 mL of methyl anthranilate (0.113 mole) was added dropwise over 10 min. Triethylamine (20 mL, 0.14 mole) was added and the solution was stirred at room temperature for 18 hr. An additional 100 mL of methylene chloride was added followed by 20 mL of water while cooling in an ice bath. The phases were mixed and the organic layer was separated. The aqueous layer was extracted with 20 mL of methylene chloride and the combined organic layers were dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 20.05 g of product as a white solid (m.p. 96°-97° C.). 1H NMR (CDCl3) δ8.66 (d, 8.0 Hz, 1H), 8.02 (dd, 8.0 Hz, 2.0 Hz, 1H), 7.53 (dt, 8.0 Hz, 2.0 Hz, 1H), 7.03 (t, 8.0 Hz, 1H), 3.98 (s, 3H, OCH3), 2.27 (s, 3H, COCH3).

Provenance & Evidence