Sodium Thiosulfate → 3-Amino-5-hydroxy-4-iodobenzoic acid

To a solution of 3-amino-5-hydroxy-benzoic acid (0.33 g, 2.16 mmol, 1.0 equiv; [CAS RN 76045-71-1]) in methanol (18 mL) at 0° C. was added within 10 min N-iodo succinimide (0.58 g, 2.59 mmol, 1.2 equiv), dissolved in methanol (3 mL). After stirring for 15 min, the reaction mixture was poured on ice and partly decolorized by addition of a 5% solution of sodium thiosulfate. The solution was extracted with ethyl acetate (3×50 mL), the combined organic phases dried over MgSO4, concentrated by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with ethyl acetate/methanol (9:1) providing 0.21 g (35%) of the title compound. 1H NMR (300 MHz, DMSO): δ 5.25 (br s, 2H), 6.61 (d, J=1.9 Hz, 1H), 6.78 (d, J=1.9 Hz, 1H), 10.16 (br s, 1H), 12.58 (br s, 1H). MS (ISP): 280.0 [M+H]+.

1. additionthe reaction mixture was poured on ice
2. extractionThe solution was extracted with ethyl acetate (3×50 mL)
3. dry with materialthe combined organic phases dried over MgSO4
4. concentrationconcentrated by evaporation under reduced pressure
5. customthe crude material purified with column chromatography on silica eluting with ethyl acetate/methanol (9:1)

ORD record

ord-e4ae248150f44f4dac2f170f0921f108

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645753B2