Hydrochloric Acid → HCID 22713809, compound

Participants

Reaction Steps

To a solution of 3-nitrophenylacetic acid, 1.0 g (5.5 mmol) in 90 mL of ethanol was added 1.0 g of PtO2 and 2 mL of 5N HCl. The mixture was hydrogenated overnight at 60° C. and 60 psi, filtered through celite and concentrated to dryness. To a solution of the residue in 15 mL of dichloromethane was added 3.0 mL (21.6 mmol) of triethylamine and 2.0 g (7.2 mmol) of 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride. The solution was stirred overnight at ambient temperature. Chloroform was added and the solution was washed with 0.5N HCl, saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated to dryness. The residue was chromatographed on silica gel using 5% acetone/dichloromethane as eluent to yield 2.0 g (66%) of the desired mixture of isomers as a white solid. 1H—NMR is consistent with structure. MS (ion spray) 423.2 (M+1).

Provenance & Evidence