Acetic Acid → 5-Amino-2-(isopropylthio)-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 16B (1.2 g, 4.7 mmol) in a mixture of ethanol (30 mL), water (5 mL), and acetic acid (3.3 mL, 5.8 mmol) was heated by a 115° C. oil bath. Iron powder (1.80 g, 32.2 mmol) was added portionwise over 1 h. The reaction mixture was cooled to rt, filtered, and washed with ethyl acetate. Sodium bicarbonate solution was added until it was basic. The reaction mixture was extracted with ethyl acetate (3×) and the combined organics were washed with saturated sodium bicarbonate and brine, dried (MgSO4), and concentrated in vacuo to give 16C (0.98 g, 93%) as a beige solid. MS (ESI) m/z 225.1 (M+H)+.

Provenance & Evidence