4-Chloro-2-nitroaniline → 3-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-hydroxy-N-methyl-benzamide (Step A, 700 mg, 4.6 mmol, 1.0 eq.) in anhydrous DMF (10 mL) was added NaH (200 mg, 5.1 mmol, 1.1 eq.). The reaction was stirred for 10 min. at RT after which 4-chloro-2-nitro-phenylamine (2.0 g, 11.6 mmol, 2.5 eq.) was added. The resulting mixture was heated to 80° C. for 4 h. The reaction was quenched with NaHCO3 (aq.), diluted with CH2Cl2 (50 mL), and washed with 1 N NaOH (25 mL). The organic layer was dried over MgSO4, filtered and concentrated. The crude was further purified by column chromatography (0-100% EtOAc in hexanes) to give pure 3-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide.

Provenance & Evidence