Dimethylformamide → HCID 58615359, compound

Participants

Reaction Steps

To a solution of 6-bromo-4-ethylsulfanyl-quinoline (1.48 g, 5.5 mmol) in THF (60 mL) was added dropwise a 2.5M solution of n-butyllithium in hexanes (2.42 mL, 6.07 mmol, 1.1 equiv.) at −70° C. During the addition, the color of the solution was turned into a dark brown and this solution was stirred for 1 h at this temperature. Then, a solution of dimethylformamide (0.848 mL, 11 mmol) in THF (5 mL) 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 (3×100 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 yellow solid which was dissolved in ethyl acetate (−10 mL) at hot condition and diluted with hexanes (−20 mL). After cooling in the refrigerator overnight, the solids were collected by filtration and washed with 10% ethyl acetate in hexanes. After drying in air, 0.614 g (51% yield) of 4-ethylsulfanyl-quinoline-6-carbaldehyde was isolated as a yellow solid: EI-HRMS m/e calcd for C12H11NOS (M+) 217.0561, found 217.0554.

Provenance & Evidence