N-Iodosuccinimide → HCID 86710119, compound

Temperature

60 °C

Ethyl 6-amino-2-methylisonicotinate (2.00 g, 11.1 mmol) was dissolved in DMF (20 mL), and the solution was stirred overnight at 60° C. after adding N-iodosuccinimide (2.50 g, 11.1 mmol). The reaction mixture was stirred at 60° C. for 5 hours after adding N-iodosuccinimide (1.25 g, 5.55 mmol). The reaction mixture was allowed to cool to room temperature, and extracted with a mixed solvent of ethyl acetate and hexane after adding a sodium hydrogen carbonate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→50/50) to give ethyl 6-amino-3-iodo-2-methylisonicotinate (1.92 g, yield 57%).

1. stirringThe reaction mixture was stirred at 60° C. for 5 hours
2. temperatureto cool to room temperature
3. extractionextracted with a mixed solvent of ethyl acetate and hexane
4. additionafter adding a sodium hydrogen carbonate aqueous solution
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was then evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→50/50)

ORD record

ord-6dbd733df6634e90a1181803ea02e55e

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000186B2