Methanol → 2-Amino-6-nitro-benzoic acid

Participants

Reaction Steps

2,6-Dinitrobenzoic acid (0.5 g, 2.36 mmol) in ethanol (5 mL) was heated to 80° C. Ammonium sulfide (40-48% in water) (0.36 mL, 2.36 mmol) was then added (the yellow solution became a bright orange suspension) the mixture was heated under reflux for 0.5 h. TLC (DCM 80%, MeOH 20%) showed a faint spot below the starting material. Ammonium sulfide (3.6 mL, 20.4 mmol) was added and the mixture became a darker orange. This mixture was then heated under reflux for 1 h after which time TLC indicated that the reaction had gone to completion. The solvents were removed under reduced pressure and then the residue washed with methanol. The methanol solution was decanted off and evaporated to dryness to afford 2-nitro-6-amino benzoic acid as a orange solid. This was then purified using flash chromatography (DCM 90%/MeOH 10%->20% MeOH over 60CV, 12 g column) to afford the desired material (0.2 g, 46%).

Provenance & Evidence