Reacción #2487394

Ecuación de reacción

lithium aluminum hydride

2-hydroxynicotinic acid

→

3-hydroxymethyl-2-pyridone

Rendimiento 32.4%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroreturned to room temperature
2. 2
   Temperaturabefore being refluxed for 8 h
3. 3
   TemperaturaThe reaction was cooled to room temperature
4. 4
   Otrowas quenched with 1.6 mL of water, 1.6 mL of 15% NaOH
5. 5
   OtroThe solvent was removed in vacuo
6. 6
   FiltraciónThe solution was filtered through celite
7. 7
   Otrothe solvent removed in vacuo

Procedimiento

In Example 1, 1.6063 g (42.33 mmol) of lithium aluminum hydride (LAH) was suspended in 100 mL of tetrahydrofuran (THF) in a 250 mL round bottom flask (RBF) under the presence of argon gas (99.999% purity) and was cooled to 0° C. in an ice bath. 5.0946 g (36.62 mmol) of 2-hydroxynicotinic acid was slowly added, and the solution returned to room temperature before being refluxed for 8 h. The reaction was cooled to room temperature and was quenched with 1.6 mL of water, 1.6 mL of 15% NaOH and an additional 4.8 mL of water. The solvent was removed in vacuo and the residue was taken up in 100 mL of refluxing ethanol. The solution was filtered through celite and the solvent removed in vacuo to produce 1.4848 g (32.40% yield) of 3-hydroxymethyl-2-pyridone. Characterization data of the product was consistent with literature.

Fuente