Methyl iodide → 4,5-Dichloro-n-methyl-2-nitroaniline

Participants

Reaction Steps

To a solution of 4,5-dichloro-2-nitroaniline (10 mmol, 2.07 g) in DMF (10 mL) was added NaH (12 mmol, 480 mg of 60% suspension in mineral oil) (exothermic, gas evolution). After 15 min MeI (20 mmol, 1.2 mL) was added. The reaction mixture was allowed to stand at ambient temperature for 1 h, then poured into a solution of saturated NaHCO3 and brine, affording the product as an orange precipitate, which was filtered, washed with water and dried in vacuo. 1H NMR (500 MHz, d6-DMSO) δ 8.27 (m, 1H), 8.22 (s, 1H), 7.25 (s, 1H), 2.96 (d, J=4.9 Hz, 3H).

Provenance & Evidence