Aniline → HCID 22124678, compound

Participants

Reaction Steps

A stirred solution of (XV, where R2 is ethyl) (100 mg, 0.52 mmol) and aniline (120 mg, 1.3 mmol) in THF (5.0 mL) under nitrogen at -78° C. was treated with a solution (1.2 mL, 1.8 mmol) of lithium diisopropylamide (1.5 M in cyclohexane), then the temperature was allowed to rise slowly to 20° C. overnight. The resulting solution was treated with 3 drops of glacial acetic acid and concentrated to a brown residue that was purified by silica gel chromatography eluting with EtOAc. The product fractions were pooled and concentrated to a solid that was crystallized to give 1-ethyl-7-phenylamino-1H -[1,6]naphthyridin-2-one (33 mg, 24%): mp (8:1 hexanes/dichloromethane) 174-175° C.

Provenance & Evidence