Lithium hydroxide, monohydrate → HCID 76902485, compound

Participants

Reaction Steps

To a colorless solution of ethyl 1-(biphenyl-2-ylmethyl)-7-bromo-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate (18) (50 mg, 0.11 mmol) in methanol (5 mL) was added solid lithium hydroxide monohydrate (22.6 mg, 0.54 mmol) at room temperature. The resulting colorless solution was stirred for 15 h at room temperature at which time LCMS analysis indicated the absence of starting material. Then, the mixture was diluted with water and the methanol was removed under vacuum. The resulting basic aqueous solution was diluted with water (˜50 mL) and 1.0N NaOH (˜10 mL) and then neutralized with 1.0N HCl. The resulting off-white solids were collected by filtration and washed with water and hexanes. After air drying, 32 mg of 1-(biphenyl-2-ylmethyl)-7-bromo-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid (19) (67% yield) was isolated as an off-white solid.

Provenance & Evidence