1,2-Dimethoxyethane → 4-(4-Cyanonaphthalene-2-yl)benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

2-Chloroquinoline-4-carbonitrile (0.20 g), 4-methoxycarbonylphenylboronic acid (0.21 g), tetrakis(triphenylphosphine)palladium (0.061 g) and sodium carbonate (0.22 g) were suspended in a mixed solvent of dimethoxyethane (2 mL) and water (0.5 mL), and the resulting mixture was stirred at 150° C. for 30 minutes using microwave reactor (Biotage). To the reaction mixture was added ethyl acetate, and the reaction mixture was filtered through a Celite pad. The filtrate was poured into water, and the organic layer was washed with water and brine. The organic layer was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 4-(4-cyanonaphthalene-2-yl)benzoic acid methyl ester (0.12 g). To a solution of this compound (0.12 g) in a mixed solvent of tetrahydrofuran (2 mL), ethanol (1 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.14 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 2 mol/L hydrochloric acid (0.35 mL). The precipitated solid was collected by filtration, washed with methanol, and dried under reduced pressure to give the title compound (0.024 g).

Provenance & Evidence