HCID 178522892, compound → HCID 178522866, compound

Participants

Reaction Conditions

Reaction Steps

N-((4-Chlorophenyl)methyl)-8-chloro-4-hydroxy-5-trifluromethyl-3-quinoline-carboxamide (2.00 g) from Example No. 59 is dissolved in glacial acetic acid (100 mL) along with NaOAc·3H2O (937 mg) and 5% palladium on carbon (666 mg). The mixture is placed under hydrogen pressure (25 psi) in a Parr hydrogenator for 3 h. The reaction mixture is filtered through a plug of celite, concentrated, suspended in water (30 mL), and filtered. The resulting solid (500 mg) and 4-chlorobenzylamine (2.13 mL) are then heated at 190° C. for 1 h. The crude product is purified by column chromatography (dichloromethane/methane, 50/1) to afford 62 mg of the title compound as a white solid.

Provenance & Evidence