Phosphorus oxychloride → HCID 86634098, compound

Participants

Reaction Conditions

Reaction Steps

4′-Bromodiphenylamine-2-carboxylic acid 3 (430 mg, 1.47 mmol) and phosphorus oxychloride (5 mL) were charged to a 25 mL rbf equipped with a reflux condenser and nitrogen bubbler. The reaction mixture was refluxed at 140° C. for 1 hour until a red colour was obtained. The excess POCl3 was removed in vacuo. The reaction mixture was carefully quenched with ice, basified with concentrated aqueous ammonia solution (the flask was kept cold with an ice bath), and extracted with chloroform. The combined organic layers were dried over magnesium sulphate, filtered and concentrated to yield the crude product. Purification by dry chromatography using a gradient elution (Hexane e Hexane:EtOAc 96:4) afforded pure 3-bromo-9-chloroacridine 4 as a cream solid (397 mg, 92%). Analyses by 1H NMR and LCMS conformed to structure.

Provenance & Evidence