Acetic Acid → HCID 14500506, compound

Participants

Reaction Steps

To a solution of 30 g of potassium carbonate dissolved in 90 mL of water and 210 mL of methanol under nitrogen was added the 11.5 g of N-(4-cyanobutyl)-N-(4-hydroxyphenyl)trifluoroacetamide and the reaction was heated at 48°-53° C. for 41/2 hours. The reaction was allowed to stand at room temperature 18 hours and then acidified with 18 mL of acetic acid. Most of the methanol was evaporated and the remaining solution was diluted with a little water and ethyl acetate and made basic with solid potassium bicarbonate. The layers were separated and the aqueous phase was reextracted with ethyl acetate. The ethyl acetate extracts were washed with saturated NaCl solution and dried over anhydrous sodium sulfate. Evaporation of the ethyl acetate solution and trituration in hexane gave a solid which was dissolved in 15 ml of acetone and filtered through a short column of silica gel using acetane-hexane (40:60). The solvent was evaporated and the resulting solid was sublimed at 0.07 mm/125° C. then recrystallized from THF-hexane to yield 2.95 g of 5-[(4-hydroxyphenyl)amino]pentanenitrile, mp 88°-90° C., (22% yield from 4-bromo-N-(4-hydroxyphenyl)butanamide).

Provenance & Evidence