Ammonia → [2,2'-Bipyridin]-6-amine

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1.O.[NH3:15]>>[N:7]1[C:2]([NH2:15])=[CH:3][CH:4]=[CH:5][C:6]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

Reactant 3

HCID 222Ammonia2×

HCID 962Water

HCID 117911522-Bromo-6-(pyridin-2-yl)pyridine

Product 1

HCID 14964570[2,2'-Bipyridin]-6-amineYield 85%

Procedure

To a mixture of 6-bromo-2,2′-bipyridine (3.0 mmol, 705 mg) and Cu2O (0.01 mmol, 1.0 mg) in glycol in autoclave NH3 was feed. The reaction was maintained under 10 atm of NH3 at 110° C. for 24 h. After cooling to room temperature, water was added and the aqueous phase was extracted with DCM. The combined organic layers were washed with brine and dried over MgSO4. After solvent evaporation, the crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=1:1 as eluent) to afford a white solid (437 mg, 85% yield). 1H NMR (500 MHz, CDCl3, ppm): 8.65 (s, 1H), 8.25 (d, 1H, J=7.9 Hz), 7.79-7.76 (m, 1H), 7.71-7.70 (m, 1H), 7.57 (t, 1H, J=7.1 Hz), 7.26 (t, 1H, J=7.1 Hz), 6.65 (d, 1H, J=7.9 Hz), 4.53 (br, 2H). 13C NMR (125 MHz, CDCl3, ppm): 157.97, 156.38, 154.57, 149.11, 138.58, 136.73, 123.31, 120.94, 111.59, 108.87.