Acetic Acid → HCID 69585623, compound

Participants

Reaction Steps

To 5-amino-2-chloro-benzoic acid methyl ester (14.0 g, 75.0 mmol) in water (100 mL) was added concentrated HCl (100 mL), followed by glacial acetic acid (100 mL). The solution was stirred at ambient temperature for 15 minutes. The reaction was then cooled to 0° C., and a solution of sodium nitrite (5.69, 82.5 mmol) in water (15 mL) was added dropwise over 30 minutes, maintaining the temperature at 0° C. The resulting reaction was stirred for 30 minutes at 0° C., then a solution of SnCl2.2H2O (50.8 g, 225 mmol) in concentrated HCl (100 mL) was added over 30 minutes, maintaining the temperature at 0° C. The slurry was stirred at 0° C. for 30 minutes, and the resulting precipitate collected by filtration, washed with water, followed by hexane. The solid was dried in a vacuum oven at 50° C. to give the title compound (16.3 g).

Provenance & Evidence