Reaktion #302869

Reaktionsgleichung

Methanol

thionyl chloride

2-aminonicotinic acid

→

2-aminonicotinic acid methyl ester

Ausbeute 55.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturto reflux
3. 3
   Temperaturthe mixture was refluxed for 19 hours
4. 4
   SonstigeThe solvent was removed under reduced pressure
5. 5
   workup.ADDITIONThe residue was carefully treated with a satured NaHCO3 solution
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   TrocknenThe organic fraction was dried over magnesium sulfate
8. 8
   Sonstigethe solvent was evaporated under reduced pressure

Vorschrift

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.).

Quelle