Dimethylformamide → 6-Quinolinecarboxaldehyde, 4-phenoxy-

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Reaction Steps

To a solution of 6-bromo-4-phenoxy-quinoline (1.12 g, 3.73 mmol) in THF (15 mL) was added dropwise a 2.5M solution of n-butyllithium in hexanes (1.64 mL, 4.10 mmol, 1.1 equiv.) at −70° C. During the addition, the color of the solution was turned into brown and this solution was stirred for 20 min at this temperature. Then, a neat dimethylformamide (0.576 mL, 7.46 mmol) was added dropwise. After addition, the mixture was allowed to warm to room temperature and stirred for 2 h. Then, the mixture was diluted with saturated ammonium chloride solution and the two layers were separated. The aqueous layer was extracted with ethyl acetate (2×75 mL). The combined organic extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under the vacuum gave the crude residue which was purified by using a Biotage silica gel column chromatography to afford 0.250 g (27% yield) of 4-phenoxy-quinoline-6-carbaldehyde as a white solid: mp 112-115° C.; EI-HRMS m/e calcd for C16H11NO2 (M+) 249.0790, found 249.0787.

Provenance & Evidence