Stannous Chloride → Methyl 3-amino-4-hydroxy-5-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 4-hydroxy-3-iodo-5-nitrobenzoate (2.99 g) in ethanol (40 mL) was added tin (II) chloride (10 g) portion wise. After stirring for 1 h at reflux, the mixture was cooled to 0° C. and quenched by saturated potassium carbonate (100 mL). The mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure to give 2.5 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.50, 7.24, 3.75.

Provenance & Evidence