Methyl 4-iodo-2-nitrobenzoate → Methyl 2-amino-4-iodobenzoate

Participants

Reaction Steps

To a solution of methyl 4-iodo-2-nitrobenzoate (2.3 g, 7.4 mmol) in DCM (5 mL) and EtOAc (5 mL) was added SnCl2-2H2O (10.8 g, 89.7 mmol). The mixture was allowed to stir for 12 h at rt. The solvents were evaporated, and the residue was partitioned between 200 mL of saturated aqueous NaHCO3 and 200 mL of DCM. The organic solution was separated and the aqueous solution was extracted with DCM (2×100 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated to give methyl 2-amino-4-iodobenzoate (1.85 g, 90%).

Provenance & Evidence