4-(4-Acetamidophenyl)-4-oxobutanoic acid → 4-(4-Aminophenyl)-4-oxobutanoic acid

Participants

Reaction Steps

A suspension of 4-(4-acetylamino-phenyl)-4-oxo-butyric acid (9.84 g, 0.0418 mol) in 1.0 M hydrocloric acid (125 mL) was heated on a steam bath for 1.5 hours, gravity filtered hot, and the filtrate allowed to cool. To the stirred solution was added 50% wt/wt sodium hydroxide (9.7 g) dropwise until pH equaled 3 to 4. The resulting precipitate was filtered, and the filtercake was washed with very dilute hydrochloric acid. The procedure was repeated on the solids with fresh 1.0 M hydrochloric acid (100 mL) to give 7.00 g of 4-(4-amino-phenyl)-4-oxo-butyric acid as a tan solid.

Provenance & Evidence