Methyl Anthranilate → Methyl 2-amino-5-iodobenzoate hydrochloride

Participants

Reaction Steps

To a solution of 25 g (0.165 mol) of methyl 2-aminobenzoate in 3 L of glacial acetic acid was added a second solution of 26.82 g (0.165 mol)iodine monochloride in 250 mL of glacial acetic acid over 20-30 min. The resulting mixture was stirred at room temperature for 24 h. The ensuing precipitate was filtered, washed with glacial acetic acid followed by diethyl ether, and dried to provide 43.2 g of the title compound, which was generally used without further purification in subsequent steps, m.p. 188-192° C.; 1H NMR (300 MHz, Me2SO--d6): δ3.79 (s,3H); 6.67 (d,1H); 7.50 (dd,1H); 7.93 (d,1H). Anal. Calcd. for C8H9NO2ICl: C, 30.65; H, 2.89; N, 4.47; O, 10.21; Cl, 11.31; I, 40.48. Found: C, 31.19; H, 2.85; N, 4.48; 0, 10.27; Cl, 11.72; I, 40.15.

Provenance & Evidence