Water → 2-Amino-5-iodobenzonitrile

Participants

Reaction Steps

A solution of iodine monochloride (16.7 g, 0.1 mol) in glacial AcOH (30 mL) as added dropwise over 15 min to a stirred solution of 2-aminobenzonitrile (11.8 g, 0.1 mol) in glacial AcOH (125 mL) at room temperature. The mixture was stirred for 3 h and then poured into H2O (1000 mL). The resulting pinkish-brown solid was filtered, washed with H2O, and dried in vacuo. Crystallization from cyclohexane-toluene (9:1) gave 2-amino-5-iodobenzonitrile (9) as translucent plates (14.9 g, 64%): mp 85-86° C. (lit. 85-86° C.); 1H NMR (CDCl3) δ 7.60 (d, J=1.6 Hz, 1H, H-6), 7.57 (dd, J=9.2 Hz, 1.6 Hz, 1H, H-4), 6.53 (d, J=9.2 Hz, 1H, H-3), 4.45 (br s; 2H, NH2). The product was used directly in the next reaction (Step 2).

Provenance & Evidence