Sodium Hydroxide → 2-Butoxy-6-methylpyridin-4-amine

Participants

Reaction Steps

2-chloro-6-methylpyridin-4-amine (36 g, 0.25 mol) and sodium hydroxide (24 g, 1 mol) were dissolved in 1-butanol (400 mL). The solution was heated at reflux for 10 h, and then cooled to rt. The reaction mixture was diluted with water (300 mL) and then extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine (500 mL), dried over sodium sulfate, and concentrated to afford 2-butoxy-6-methylpyridin-4-amine. 1H NMR (400 MHz, CDCl3) δ 6.05 (d, J=0.6 Hz, 1H), 5.75 (d, J=0.6 Hz, 1H), 4.18 (t, J=6.4 Hz, 1H), 2.30 (s, 3H), 1.71 (m, 2H), 1.48 (m, 2H), 0.98 (t, J=7.6 Hz, 3H). LRMS calc'd for (C10H16N2O) [M+H]+, 181; found 181.

Provenance & Evidence