Hydrochloric Acid → HCID 22139706, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.4 mL HCl in 24 mL H2O was heated to the boiling point and poured into 2.4 g (0.008 mol) of 5-(2,4-difluoro-phenoxy)-6-methoxy-quinolin-8-ylamine, then stirred while hot to dissolve as much solid as possible. The solution was cooled in an ice-salt mixture. When the temperature reached 15° C., 2.5 mL of conc. HCl were added to the reaction mixture. At 10° C. a solution of NaNO2 (1.1 g, 0.016 mol in 2 mL of water) was added dropwise during 10 min. The reaction mixture was stirred at 5–10° C. for 30 min., treated with ice-cold 30% H3PO4, and cooled at 0° C. overnight. After stirring for an additional 8 hours. at room temperature, the reaction mixture was neutralized with 1N NaOH, extracted with CH2Cl2, and the organic layer was dried (MgSO4). Solvent removal, followed by HPLC, eluting with 10–20% EtOAc/Hexane gave 1.5 g (66%) of 5-(2,4-difluoro-phenoxy)-6-methoxy-quinoline, which crystallized at room temperature.

Provenance & Evidence