Réaction #1529964

Équation de réaction

NaHCO3

water

2-bromo-3-methoxy-6-nitropyridine

SnCl2.2H2O

→

6-bromo-5-methoxypyridin-2-amine

Rendement 65.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was heated
2. 2
   Températureat reflux for 2H
3. 3
   Extractionextracted with ethyl acetate (50×3 mL)
4. 4
   SéchageThe combined organic layers were dried over Na2SO4
5. 5
   Autreevaporated in vacuo
6. 6
   Autrepurified by chromatography on silica gel (20% ethyl acetate in petroleum ether)

Mode opératoire

To a solution of 2-bromo-3-methoxy-6-nitropyridine (2.0 g, 8.6 mmol) in ethanol (20 mL) was added SnCl2.2H2O (3.9 g, 17 mmol) at room temperature. The reaction was heated at reflux for 2H. After cooling to room temperature, the reaction mixture was poured into water (50 mL), basified to pH to 8 with saturated NaHCO3 and extracted with ethyl acetate (50×3 mL). The combined organic layers were dried over Na2SO4, evaporated in vacuo and purified by chromatography on silica gel (20% ethyl acetate in petroleum ether) to afford 6-bromo-5-methoxypyridin-2-amine (1.1 g, 65%). 1H-NMR (300 MHz, CDCl3) δ 7.09 (d, J=8.4, 1H), 6.43 (d, J=8.4, 1H), 4.27 (br s, 2H), 3.82 (s, 3H).

Source