Chloride → 2,6-Dichloro-3-methylaniline

Participants

Reaction Steps

N-(2,6-Dichloro-3-methylphenyl)acetamide (22 g) was suspended in HCl (5.0 N, 100 mL), H2O (300 mL) and propanol (or AcOH, 20-50 mL). The mixture was refluxed for several hr after which the solution was cooled, chloride (3×200 mL). The organic extractions were combined, washed with water, dried over MgSP4, and concentrated to give 16 g of product as a low melting solid (m.p. 36°-38° C.). 1H NMR (CCl4) δ6.97 (d, 9.0), 6.46 (d, 9.0 Hz, 1H), 2.28 (s, 3H, CH3)

Provenance & Evidence