反应 #302869

反应方程式

Methanol

thionyl chloride

2-aminonicotinic acid

→

2-aminonicotinic acid methyl ester

收率 55.0%

反应条件

后处理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux
3. 3
   温度the mixture was refluxed for 19 hours
4. 4
   其他The solvent was removed under reduced pressure
5. 5
   workup.ADDITIONThe residue was carefully treated with a satured NaHCO3 solution
6. 6
   萃取extracted with ethyl acetate
7. 7
   干燥The organic fraction was dried over magnesium sulfate
8. 8
   其他the solvent was evaporated under reduced pressure

实验过程

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.).

来源