Reacción #465956

Ecuación de reacción

2-ethylhexanol

sulfuric acid

4-amino-3,6-dichloro-pyridine-2-carboxylic acid

→

2-ethylhexyl 4-amino-3,6-dichloropyridine-2-carboxylate

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter heating
2. 2
   Otrothe reaction
3. 3
   Temperaturato reflux overnight
4. 4
   Temperaturathe reaction mixture was cooled
5. 5
   Extracciónextracted with ethyl acetate (75 mL)
6. 6
   LavadoThe organic phase was washed with sodium bicarbonate (75 mL)
7. 7
   Secadodried (Na2SO4)
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe resulting solid was recrystallized out of dichloromethane and hexane
10. 10
    Filtraciónfiltered

Procedimiento

To a solution of 2-ethylhexanol (10 mL) and sulfuric acid (1 mL) was added 4-amino-3,6-dichloro-pyridine-2-carboxylic acid (0.0097 mol, 2.0 g). After heating the reaction to reflux overnight, the reaction mixture was cooled, poured into water (75 mL), and extracted with ethyl acetate (75 mL). The organic phase was washed with sodium bicarbonate (75 mL), dried (Na2SO4), and concentrated. The resulting solid was recrystallized out of dichloromethane and hexane and filtered to give 2-ethylhexyl 4-amino-3,6-dichloropyridine-2-carboxylate (0.0074 mol, 2.36 g) as a crystalline solid (mp 55° C.). 1H NMR (CDCl3): δ 0.9 (7 H, m), 1.3 (7 H, m), 1.7 (1 H, m), 4.3 (2 H, d), 5.1 (2 H, bs), 6.7 (1 H, s).

Fuente