2-Aminobenzonitrile → 2-Amino-5-iodobenzonitrile

Participants

Reaction Conditions

Reaction Steps

2-Aminobenzonitrile (2.0 g, 16.9 mmol, 1 equiv.) was dissolved in dry N,N-dimethylformamide (30 mL), and the solution was cooled to 0° C. A solution of N-iodosuccinimide, NIS (3.81 g, 16.9 mmol, 1 equiv.) in 30 mL of DMF was added dropwise with an addition funnel. After the NIS/DMF solution was, added, the ice bath was removed, and the reaction was stirred at room temperature overnight. The reaction was quenched by pouring into 3N NaOH (300 mL) and diluted with an additional 200 mL of water. 2-Amino-5-iodobenzonitrile formed as a precipitate, which was collected by filtration.

Provenance & Evidence