Hydrochloric Acid → 5-Chloro-2-hydroxy-N-[(4-phenoxyphenyl)methyl]benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-chlorocsalicyclic acid in anhydrous DMF (5 mL) was added CDI (0.167 g, 1.043 mmol), at 25° C. under nitrogen atmosphere. The reaction mixture was stirred for another 2 h at 25° C. To the above reaction mixture 4-phenoxy benzylamine was added and stirring continued overnight. At the end of this period 2N HCl (20 mL) was added and extracted with ethyl acetate (2×20 mL). The combined ethyl acetate layer was washed with water (2×30 mL), dried (Na2SO4), filtered and solvent was evaporated. The resulting crude material was chromatographed over silica gel using mixture of ethyl acetate and hexanes (3:7) to give title product (0.121 g, 27%). 1H NMR (CDCl3) δ 4.60 (d, 2H), 6.44 (bs, 1H), 6.90-7.37 (m, 12H), 12.21 (s, 1H),

Provenance & Evidence