3-Phenylpyridine → 5-Phenyl-2-pyridinamine
Reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2-:13].[Na+]>C1(C)C=CC(C)=CC=1>[NH2:13][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=[CH:10][N:9]=1.[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][N:9]=1Participants
5
Reactant 2
Product 2
Reagents, catalysts & solvents 1
Procedure
2-amino-3-phenyl pyridine was prepared as follows: 3-phenyl pyridine (300 mg, 2 mmol) was dissolved in para-xylene (6 ml), and sodamide (84 mg, 2.1 mmol) was then added. The reaction mixture was heated to reflux temperature for 8 hours. The reaction mixture was cooled, poured onto ice/water (25 ml), and extracted with dichloromethane. The organic extracts were washed with water and brine, and dried over anhydrous sodium sulphate. The sodium sulphate was removed by filtration, and the filtrate was evaporated to dryness and recrystallized from a mixture of diethyl ether and petroleum ether to provide 2-amino-5-phenyl pyridine (95 mg). The mother liquors from the crystallization were evaporated to dryness and subjected to purification by column chromatography (silica), thereby eluting the solvent ethyl acetate:petroleum ether (30:70). The desired product, 2-amino-3-phenyl pyridine, was obtained as a fine yellow powder (15 mg).