Aluminium lithium hydride → HCID 68839509, compound

Participants

Reaction Steps

To a solution of 4-(pyridin-3-ylsulfamoylmethyl)benzoic acid methyl ester (1.91 g, 6.23 mmol) in THF (60 mL) at 0° C. was added a 1 M solution of LiAlH4 in THF (13.7 mL, 13.7 mmol), and the mixture was warmed to room temperature. After stirring for 10 minutes, the mixture was heated to reflux temperature for 3 hours. The reaction mixture was cooled to 0° C. and quenched with saturated Na2SO4 aqueous solution (1.9 mL). The mixture was neutralized with 1 N HCl solution (13.7 mL), and then THF was evaporated under reduced pressure. The residue was diluted with water (70 mL) and extracted with CHCl3 (50 mL×3). The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by MPLC on silica gel (6% MeOH in EtOAc) to afford the titled compound (1.43 g, 83%) as a pale yellow solid.

Provenance & Evidence