2-Amino-4-butylpyridine

2-Amino-4-butylpyridine

A mixture of 4-butylpyridine (5.0 g, 37.0 mmol) and 95% sodium amide (1.7 g, 40.7 mmol) in xylene (10 ml) was heated at 150° C. for 18 hours. The cooled mixture was diluted with ether (100 ml) and extracted with 2N hydrochloric acid (twice). The aqueous extracts were basified using sodium hydroxide solution, and re-extracted with ether. These combined organic extracts were dried (MgSO₄) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (97:3:0.15) as eluant, to afford the title compound as a crystalline solid, 2.1 g, 38%; 

¹H NMR (CDCl₃, 300 MHz) δ: 0.96 (t, 3H), 1.38 (m, 2H), 1.60 (m, 2H), 2.52 (t, 2H), 4.38 (bs, 2H), 6.38 (s, 1H), 6.55 (d, 1H), 7.98 (d, 1H);

 Anal. Found: C, 72.01; H, 9.47; N, 18.53. C₉H₁₄N₂requires C, 71.96; H, 9.39; N, 18.65%.

2-Amino-4-butylpyridine

2-Amino-4-butylpyridine

A mixture of 4-butylpyridine (5.0 g, 37.0 mmol) and 95% sodium amide (1.7 g, 40.7 mmol) in xylene (10 ml) was heated at 150° C. for 18 hours. The cooled mixture was diluted with ether (100 ml) and extracted with 2N hydrochloric acid (twice). The aqueous extracts were basified using sodium hydroxide solution, and re-extracted with ether. These combined organic extracts were dried (MgSO₄) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (97:3:0.15) as eluant, to afford the title compound as a crystalline solid, 2.1 g, 38%;

 ¹H NMR (CDCl₃, 300 MHz) δ: 0.96 (t, 3H), 1.38 (m, 2H), 1.60 (m, 2H), 2.52 (t, 2H), 4.38 (bs, 2H), 6.38 (s, 1H), 6.55 (d, 1H), 7.98 (d, 1H);

Anal. Found: C, 72.01; H, 9.47; N, 18.53. C₉H₁₄N₂requires C, 71.96; H, 9.39; N, 18.65%.