2-Amino-6-chloro-4-picoline synthesis

Yield:51564-92-2 82%

Reaction Conditions:

Stage #1: N-(6-chloro-4-methylpyridin-2-yl)pivalamidewith hydrogenchloride;water at 90; for 6 h;
Stage #2: with sodium hydroxide in water at 20; pH=10;

Steps:

J.d

Step d: 6-Chloro-4-methylpyridin-2-amine; A solution of N-(6-chloro-4-methylpyridin-2-yl)pivalamide (500 mg, 2.21 mmol) in HCl (40 mL, 6 M) was stirred for 6 hours at 90 ⁰C. The mixture was cooled to room temperature and neutralized with NaOH to pH 10. The mixture was extracted with ethyl acetate, evaporated under vacuum, and purified by chromatography on silica gel (5% ethyl acetate in petroleum ether) to afford 6-chloro-4-methylpyridin-2-amine (257 mg, 82%). ¹H νMR (CDCl₃, 300 MHz) δ 6.52 (s, IH), 6.26 (s, IH), 2.23 (s, 3H).

References:

WO2008/141119,2008,A2 Location in patent:Page/Page column 86-87