Reaction #465956

Reaction equation

2-ethylhexanol

sulfuric acid

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

→

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

Solvents

water

Conditions

Workup

1. 1
   TemperatureAfter heating
2. 2
   Otherthe reaction
3. 3
   Temperatureto reflux overnight
4. 4
   Temperaturethe reaction mixture was cooled
5. 5
   Extractionextracted with ethyl acetate (75 mL)
6. 6
   WashThe organic phase was washed with sodium bicarbonate (75 mL)
7. 7
   Dryingdried (Na2SO4)
8. 8
   Concentrationconcentrated
9. 9
   OtherThe resulting solid was recrystallized out of dichloromethane and hexane
10. 10
    Filtrationfiltered

Procedure

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).

Source