Isatoic Anhydride → 2-amino-benzoic acid N'-pyridin-2-yl-hydrazide

Participants

Reaction Steps

A mixture of isatoic anhydride (3.51 g, 2.15 mmol) and 2-hydrazinopyridine (2.40 g, 2.20 mmol) in 35 ml of EtOH was refluxed for 17 hours. After refluxing for 15 minutes, the suspension turned into a brown solution and gas evolution was observed. At the end of the 17 hour period, the reaction mixture was cooled to room temperature and the brown solution was concentrated on a rotary evaporator. The residue was chromatographed on silica gel with 65% EtOAc in hexanes. The fractions containing the product were collected and concentrated. The solid was triturated with ether (100 ml) for 15 minutes and collected by filtration. It was air-dried to give 2.68 g of 2-amino-benzoic acid N′-pyridin-2-yl-hydrazide (Intermediate 9) as a white solid. MS (APCI): 229 (M+1, 100%).

Provenance & Evidence