Hydrochloric Acid → 5-Cyano-3-methoxypicolinic acid

Temperature

0 °C

In a 1-L flask, the methyl 5-cyano-3-methoxypicolinate (step 2, 4.51 g, 23.5 mmol) was taken up in THF (74 mL). The suspension was cooled to 0° C., and sodium hydroxide (1M, 24.64 mL, 24.64 mmol) was added. After 1 h, the reaction was concentrated under reduced pressure. The residue was taken up in 100 mL of water, and the aqueous phase was extracted with diethyl ether (50 mL), which was discarded. The aqueous phase was acidified with HCl (5M, 5.16 mL, 25.8 mmol). The aqueous phase was extracted with DCM (11×150 mL). The combined organic extracts were dried over MgSO4 and the filtrate was concentrated under reduced pressure to afford the title compound as a white solid. MS m/z=179 [M+H]+. Calculated for C8H6N2O3: 178. 1H NMR in CDCl3 δ: 8.48 (d, 1H, J=1.6), 7.71 (d, 1H, J=1.6), 4.08 (s, 3H).

1. concentrationthe reaction was concentrated under reduced pressure
2. extractionthe aqueous phase was extracted with diethyl ether (50 mL), which
3. extractionThe aqueous phase was extracted with DCM (11×150 mL)
4. dry with materialThe combined organic extracts were dried over MgSO4
5. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-3f83adb67ce24c84babc512c40148e5f

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2