ChemicalBook CAS DataBase List 2-Amino-6-chloro-4-picoline

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

5synthesis methods

Product Name:2-Amino-6-chloro-4-picoline
CAS Number:51564-92-2
Molecular formula:C6H7ClN2
Molecular Weight:142.59

Propanamide, N-(6-chloro-4-methyl-2-pyridinyl)-2,2-dimethyl-

1004294-60-3

51564-92-2

Step d: Synthesis of 6-chloro-4-methylpyridin-2-amine; N-(6-chloro-4-methylpyridin-2-yl) neopentanamide (500 mg, 2.21 mmol) was dissolved in 6M hydrochloric acid solution (40 mL) and the reaction was stirred at 90 °C for 6 h. The reaction was carried out at 90 °C for 2 h. The reaction was carried out at 90 °C for 1 h. The reaction was carried out at 90 °C for 2 h. The reaction was carried out at 90 °C for 2 h. The reaction was carried out at 90 °C for 2 h. The reaction was carried out at 90 °C for 2 h. The reaction was carried out at 90 °C for 2 h. Upon completion of the reaction, the mixture was cooled to room temperature and neutralized with sodium hydroxide solution to pH 10. Subsequently, the mixture was extracted with ethyl acetate, the organic phases were combined and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a mixed solution of petroleum ether and ethyl acetate (95:5, v/v) to afford 6-chloro-4-methylpyridin-2-amine (257 mg, 82% yield). The product was characterized by 1H NMR (CDCl3, 300 MHz): δ 6.52 (s, 1H), 6.26 (s, 1H), 2.23 (s, 3H).

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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

39621-00-6 Synthesis