Hydrochloric Acid → 4-(Acetylamino)-3-((Hydroxyacetyl)Amino)Benzoic Acid

Participants

Reaction Steps

Compound 17 (0.200 g, 0.652 mmol) was dissolved in 0.1N NaOH (7.93 mL) and stirred at room temperature for 2 hours. The alkaline aqueous layer was acidified to pH 2 with cone HCl, extracted with ethyl acetate (2×15 mL), and the extracts were dried (Na2SO4) and concentrated on a rotary evaporator to give only 8 mg of 109. The aqueous layer was concentrated on a rotary evaporator to 25% of the original volume, cooled, and the solid which separated was filtered. This was dried under vacuum to give 109 (60 mg, 58% yield) as a white solid: mp 214°-215° C.

Provenance & Evidence