Ammonia → 5-Phenyl-2-pyridinamine

A solution of 2-chloro-5-phenylpyridine (4.0 g., 0.021 mole) in dry diethyl ether (160 ml.) was added dropwise to a solution of sodium (3.39 g., 0.15 g-atom) in liquid ammonia (160 ml.) containing ferrous nitrate hexahydrate (0.095 g.). The resulting suspension was allowed to reflux for 4 hours. Ammonium chloride was added and the ammonia allowed to evaporate. The residue was treated with 5% aqueous sodium hydroxide (5 ml.). The mixture was filtered. The aqueous layer was extracted with ether (2×100 ml.). The combined ethereal layers were washed with brine and dried over sodium sulfate. The solution was concentrated and the residue recrystallized from methylcyclohexane. The product was triturated with chloroform (100 ml.). The mixture was filtered and the filtrate evaporated to give 2-amino-5-phenylpyridine (1.3 g., 36%), m.p. 133°-135° (lit. m.p. 133° in Chem. Ber., 91, 247 (1958).

1. temperatureto reflux for 4 hours
2. customto evaporate
3. additionThe residue was treated with 5% aqueous sodium hydroxide (5 ml.)
4. filtrationThe mixture was filtered
5. extractionThe aqueous layer was extracted with ether (2×100 ml.)
6. washThe combined ethereal layers were washed with brine
7. dry with materialdried over sodium sulfate
8. concentrationThe solution was concentrated
9. customthe residue recrystallized from methylcyclohexane
10. customThe product was triturated with chloroform (100 ml.)
11. filtrationThe mixture was filtered
12. customthe filtrate evaporated

ORD record

ord-878e05fb8f8743fbbd6ca25b2b784ae3

Source dataset

uspto-grants-1980_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04192944