Methyl iodide → Methyl 5-chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

To a suspension of 5-chloro-2-hydroxynicotinic acid (2.0 g, 12 mmol) and cesium carbonate (8.2 g, 26 mmol) in 50 mL DMF was added MeI (1.6 ml, 26 mmol). The reaction was allowed to stir for approximately 12 h. The cloudy yellow mixture was added to EtOAc/water. The organic layer was removed and the aqueous layer was extracted three times with EtOAc. The combined organic layers were washed once with water and brine, dried with Na2SO4, filtered, and concentrated to give an orange-yellow solid. The material was partitioned between 1N HCl and EtOAc. The organic layer was washed twice with 1N HCl, dried with Na2SO4, filtered, and concentrated to give the desired product as an orange solid. MS (m/z): 202.0 (M+H)+. Calc'd for C8H8ClNO3: 201.61.

1. customThe organic layer was removed
2. extractionthe aqueous layer was extracted three times with EtOAc
3. washThe combined organic layers were washed once with water and brine
4. dry with materialdried with Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give an orange-yellow solid
8. customThe material was partitioned between 1N HCl and EtOAc
9. washThe organic layer was washed twice with 1N HCl
10. dry with materialdried with Na2SO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-d67995f741e54ed285268ef3321a37bc

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557996B2