Potassium Iodide → 2-Iodo-7-nitronaphthalene

Participants

Reaction Conditions

Reaction Steps

A suspension of 7-nitro-2-aminonaphthalene (260 mg, 1.38 mmol) in concentrated HCl (10 mL) is cooled to 0° C. Sodium nitrite (105 mg, 1.53 mmol) is added in portions and the reaction is allowed to stir at 0° C. for 30 minutes. A solution of iodide (175 mg, 253.8 mmol) and potassium iodide (459 mg, 2.76 mmol) in water (5 mL) is added dropwise. After stirring at 0° C. for 1 hour, the solid is removed by filtration. The solid is dissolved in EtOAc and washed with sodium metabisulfite solution, water and brine. The organic layer is dried (Na2SO4) and the solvents evaporated to give 2-iodo-7-nitronaphthalene as an orange solid.

Provenance & Evidence