Ethyl Glycolate → Ethyl 2-[(6-chloro-3-nitro-2-pyridinyl)oxy]acetate

A stirred solution of 2,6-dichloro-3-nitropyridine (15 g, 78 mmol) and ethyl glycolate (8.1 mL, 86 mmol) in 1,4-dioxane (150 mL) was cooled to 10° C. NaH (60% dispersion in oil) (3.42 g, 86 mmol) was added batchwise. The mixture was then allowed to stir for 6 hours at ambient temperature. The mixture was then cooled (˜10° C.) and treated with saturated aqueous ammonium chloride solution. Water was added until all the solid had dissolved and the mixture was extracted with EtOAc. The EtOAc layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by crystallisation from EtOH (80 mL) to give (6-chloro-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (8.55 g). [M+H]+ 261

1. temperatureThe mixture was then cooled (˜10° C.)
2. dissolutionhad dissolved
3. extractionthe mixture was extracted with EtOAc
4. washThe EtOAc layer was washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by crystallisation from EtOH (80 mL)

ORD record

ord-591f612ea2054d26a61d83160fb26458

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09155743B2