Potassium Iodide → Quinoline-6-carboxylic acid oxiranylmethyl ester

Quinoline-6-carboxylic acid (1 g; 5.78 mmol) is dissolved in DMF (10 mL) at ambient temperature. Epichlorohydrin (0.4517 mL; 5.59 mmol) is added followed by mortar ground potassium carbonate (0.80 g; 5.79 mmol). The mixture is stirred at ambient temperature for 48 hours. Potassium iodide (96 mg; 0.58 mmol) is added and stirring is continued at ambient temperature for 24 hours. The mixture is heated to 60° C. and maintained for 72 hours. After cooling, the mixture is poured onto water (700 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts are washed successively with water (100 mL), and brine (50 mL), then dried over MgSO4, filtered, and concentrated in vacuo at 30C. The residue is purified via silica gel chromatography with gradient elution (20%→67% ethyl acetate in hexanes) affording the desired product (270 mg) as a white solid. ESMS: MH+ 230.0 (base).

1. stirringstirring
2. waitis continued at ambient temperature for 24 hours
3. temperatureThe mixture is heated to 60° C.
4. temperaturemaintained for 72 hours
5. temperatureAfter cooling
6. additionthe mixture is poured onto water (700 mL)
7. extractionextracted with ethyl acetate (3×100 mL)
8. washThe combined organic extracts are washed successively with water (100 mL), and brine (50 mL)
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo at 30C
12. customThe residue is purified via silica gel chromatography with gradient elution (20%→67% ethyl acetate in hexanes)

ORD record

ord-c7e223c734fb46bdb4fe564c82b14a4c

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07476680B2