Pyridine → 2,5-Dihydroxybenzonitrile

Participants

Reaction Steps

Trifluoroacetic anhydride (3.06 mL, 22 mmoles) was added dropwise to a stirred, ice-cooled solution of 34 (770 mg, 5.0 mmoles) in 10 mL of dry THF and anhydrous pyridine (3.23 mL, 40 mmoles) at such a rate that the temperature was kept below 5° C. The addition was over in 30 minutes. The reaction mixture was then allowed to warm to room temperature and stirred for another 16 hr. 650 mL of CH2Cl2 was added and the organic solution was washed with water (3×10 mL) and saturated brine (3×15 mL), dried on Na2SO4 and evaporated under reduced pressure. The crude product was applied to silica gel (230-400 mesh, ethyl acetate) to yield 462 milligrams (68%) of 20.

Provenance & Evidence