Anthranilic Acid → HCID 21699698, compound

Participants

Reaction Steps

Anthranilic acid (9.6 g, 70 mmol) and 1-benzyl-4-piperidone (13.2 g, 70 mmol) were suspended in phosphorus oxychloride (65.2 ml, 700 mmol), and the suspension was heated under reflux for 4 hours. The excess phosphorus oxychloride was removed by distillation and the concentrated residue was carefully added to 28% aqueous ammonia under ice-cooling and extracted with chloroform. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate/methanol=30:10:1) to obtain the desired compound (13 g, 60%) as a light-yellowish-white substance.

Provenance & Evidence