2-Chloroaniline → 4-Chloro-2-(2-chloro-phenylamino)-benzoic acid

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round bottom flask, 2-bromo-4-chloro-benzoic acid (10 g, 42.5 mmol), 2-chloroaniline (8.49 g, 7.0 mL, 66.6 mmol), potassium carbonate (9.39 g, 68.0 mmol), copper (0.092 g, 1.44 mmol) and copper (I) oxide (0.126 g, 0.88 mmol) were combined with 2-ethoxyethanol (20 mL). The mixture was heated to 130° C. for 4 hr. The mixture was cooled to room temp. and 150 mL of water was added. The slurry was stirred at room temperature for 2 days. The slurry was filtered and rinsed with 2-ethoxyethanol. The pH of the filtrate was adjusted to 7 using 4N HCl and the solid was filtered off. The green solid was then air-dried for 4 hr. to give 4-chloro-2-(2-chloro-phenylamino)-benzoic acid (3.5 g, 29% yield). The material was used in the next step without further purification. MS calcd. for C13H9Cl2N3O2 [(M−H)−1]280.0, obsd. 280.0.

Provenance & Evidence