Hydrochloric Acid → HCID 10430792, compound

Participants

Reaction Steps

A stirred solution of phenanthridine (7.16 g, 40 mmol) in anhydrous diethyl ether (40 mL) was cooled to −30° C., and treated drop-wise under nitrogen via syringe with a solution of 1.4 M methyllithium in diethyl ether (30 mL, 42 mmol). The yellow solution was warmed to room temperature and stirred for 15 minutes. The mixture was cooled to −78° C., and treated with 5-(chlorosulfonyl)-2-hydroxybenzoic acid (9.47 g, 40 mmol) as a solid in a single aliquot. The reaction mixture was diluted with anhydrous tetrahydrofuran (40 mL), warmed to room temperature, and a solution of N,N-diisopropylethylamine (25.85 g, 200 mmol) in anhydrous dimethylformamide (40 mL) was added. After stirring at room temperature overnight, the reaction mixture was poured into a 1 N hydrochloric acid solution, and extracted with ethyl acetate. The organic phase was washed sequentially with a 1 N aqueous hydrochloric acid solution, water, and a saturated, aqueous, sodium chloride solution. After drying over anhydrous sodium sulfate, the organic phase was filtered and the solvent evaporated in vacuo to yield a crude yellow solid (3.4 g, 21%). The crude solid (1.0 g) was purified by reverse phase preparative chromatography on a Primesphere® 10 C-18 column (25 cm×5 cm), eluting with 56% acetonitrile in water with 0.1% trifluoroacetic acid at a flow rate of 90 mL/min. After evaporation of the acetonitrile solvent, the aqueous phase was extracted with ethyl acetate. The organic phase was washed sequentially with water and a saturated, aqueous, sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent evaporated in vacuo to a colorless solid. Crystallization of the colorless solid from a mixture of diethyl ether-hexane yielded the title compound (0.46 g, 1.16 mmol) as a homogeneous, colorless, crystalline solid, m.p. 225-230° C.;

Provenance & Evidence