Sulfuric Acid → 2-Chloro-5iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Participants

Reaction Steps

To a solution of amino amide from Example 55 (200 mg) in 75% aqueous tetrahydrofuran 1/3 (10 ml) at −5 C. was added sulphuric acid (0.2 ml) followed by sodium nitrite (0.042 g) in water (1 ml). The resulting reaction mixture was stirred for 40 min before potassium iodide (0.136 g) was added. The reaction mixture was heated at 90 C. for 1 hour, cooled to room temperature and diluted with water and extracted with ethyl acetate. The organic layers were separated and dried over magnesium sulphate. The filtered solution was concentrated under reduced pressure and the crude material purified over silica eluting with hexaneslethyl acetate to give the title compound as a white solid (0.23 g).

Provenance & Evidence