Chemical Properties
Beige Crystalline Solid
Uses
A product from the pyrolysis of phenylalanine
Definition
ChEBI: 5-Phenyl-2-pyridinamine is a phenylpyridine.
Safety Profile
Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.
Synthesis
The general procedure for the synthesis of 2-amino-5-phenylpyridine from 2-chloro-5-phenylpyridine is as follows:
1. a solution was prepared by dissolving 2-chloro-5-phenylpyridine (4.0 g, 0.021 mol) in anhydrous ether (160 ml).
2. the above solution was slowly added dropwise to a solution of liquid ammonia (160 ml) containing sodium (3.39 g, 0.15 g atoms) and ferrous nitrate hexahydrate (0.095 g).
3. The resulting suspension was heated to reflux for 4 hours.
4. Upon completion of the reaction, ammonium chloride was added and the ammonia was allowed to evaporate naturally.
5. The residue is treated with a 5% aqueous sodium hydroxide solution (5 mL).
6. Filter the mixture to separate the solids from the liquid.
7. Extract the aqueous layer with ether (2 x 100 ml) and combine the ether layers.
8. Wash the combined ether layers with brine and dry with sodium sulfate.
9. The dried ether solution was concentrated to give the crude product.
10. the crude product was recrystallized with methylcyclohexane. 11.
11. The recrystallized product was ground with chloroform (100 ml).
12. The mixture was filtered and the filtrate was evaporated to give the final product 2-amino-5-phenylpyridine (1.3 g, 36% yield) with a melting point of 205 °C.
Melting points of 133°-135° have been reported in the literature (Chem. Ber., 91, 247 (1958)).
References
[1] Patent: US4122274, 1978, A
