Water → 6-(4-Fluorobenzyl)picolinic acid

Participants

Reaction Conditions

Reaction Steps

6-(4-Fluorobenzyl)picolinonitrile (24 mg, 113 μmol; CAN 1237431-32-1) and powdered sodium hydroxide (18.1 mg, 452 μmol) were dissolved in water (3 mL). The reaction mixture was heated to 90° C. for 2.5 h. Additional powdered sodium hydroxide (18.1 mg, 452 μmol) was added and heating was continued for another 2.5 h. The reaction mixture was poured onto 25 mL ice/0.1N HCl and extracted with EtOAc (2×20 mL). The combined organic layers were washed with ice water/brine (25 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (21 mg, 80%) as light yellow oil which was used in the next step without further purification. MS (EI): m/e=230.1 [M−H]−.

Provenance & Evidence