Sodium Iodide → Methyl 4-iodo-2-methylnicotinate

Temperature

80 °C

To a solution of methyl 4-chloro-2-methylnicotinate (6.00 g, 32.3 mmol) in acetonitrile (80 mL) was added acetyl chloride (3.45 mL, 48.5 mmol) followed by sodium iodide (48.5 g, 323 mmol). The reaction mixture was heated at 80° C. for 16 hrs. The reaction mixture was evaporated to dryness and the residue was adjusted to pH 6 by adding saturated potassium carbonate solution. The product was extracted with dichloromethane (250 mL). The organic phase was washed with brine (2×100 mL), dried over Na2SO4, and concentrated under reduced pressure to afford methyl 4-iodo-2-methylnicotinate (2.00 g, 7.22 mmol, 22% crude yield) as colorless semisolid which was carried on without further purifications. LC/MS (ESI) m/e 278.0 [(M+H)+, calcd for C8H9INO2 278.0]; LC/MS retention time (method C): tR=2.13 min.

1. customThe reaction mixture was evaporated to dryness
2. additionby adding saturated potassium carbonate solution
3. extractionThe product was extracted with dichloromethane (250 mL)
4. washThe organic phase was washed with brine (2×100 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-07bf48f296c6406891da134616c43eec

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901305B2