Reacción #302869

Ecuación de reacción

Methanol

thionyl chloride

2-aminonicotinic acid

→

2-aminonicotinic acid methyl ester

Rendimiento 55.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturato reflux
3. 3
   Temperaturathe mixture was refluxed for 19 hours
4. 4
   OtroThe solvent was removed under reduced pressure
5. 5
   workup.ADDITIONThe residue was carefully treated with a satured NaHCO3 solution
6. 6
   Extracciónextracted with ethyl acetate
7. 7
   SecadoThe organic fraction was dried over magnesium sulfate
8. 8
   Otrothe solvent was evaporated under reduced pressure

Procedimiento

42.4 g (356.4 mmol, 26 ml) thionyl chloride was added dropwise to a suspension of 15.0 g (108.6 mmol) 2-aminonicotinic acid in 150 ml abs. Methanol, while cooling. The mixture was heated to reflux and the mixture was refluxed for 19 hours. The evolving SO2 was scrubbed. The solvent was removed under reduced pressure after cooling down to room temperature. The residue was carefully treated with a satured NaHCO3 solution and extracted with ethyl acetate. The organic fraction was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. 9.13 g (55%) of 2-aminonicotinic acid methyl ester was isolated as a pale yellow solid (m.p. 83° C.).

Fuente