2-Aminopyridine → HCID 14476377, compound

Participants

Reaction Steps

Para-toluenesulphonic acid (50 mg) is added to an agitated solution of 2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-3-hydroxy1-isoindolinone (6 g) and 2-aminopyridine (2 g) in xylene (150 cc) at a temperature close to 20° C. in a Dean Stark apparatus. Agitation is continued for 5 hours at a temperature close to 135° C. After cooling to a temperature close to 20° C., the solution is washed with aqueous sodium bicarbonate solution (2×100 cc) then with distilled water (2×50 cc). The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 80° C. The precipitate is recrystallized from boiling acetonitrile (45 cc). 3.7 g of 3-(2-pyridylamino)-2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone are obtained, melting at 153° C.

Provenance & Evidence