Ammonium Chloride → Methyl 3-amino-2-chlorobenzoate

Participants

Reaction Steps

To the solution of 213A: (1 g, 4.64 mmol) in MeOH (23.19 ml) was added ammonium chloride (2.481 g, 4.64 mmol) and zinc dust (1.516 g, 23.19 mmol). The reaction was stirred at rt for 2 h, then warmed to 60° C. for 1 h. The reaction was filtered through a pad of Celite, rinsing with MeOH. The filtrate was concentrated. The residue was partitioned between EtOAc and water and the layers were separated. The organic layer washed with sat. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. Purification by silica gel chromatography afforded 213B (0.85 g, 99% yield) as a yellow oil. MS (ESI) m/z: 186.0 (M+H)+.

Provenance & Evidence