Reaction #2487394

Reaction equation

lithium aluminum hydride

2-hydroxynicotinic acid

→

3-hydroxymethyl-2-pyridone

Yield 32.4%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherreturned to room temperature
2. 2
   Temperaturebefore being refluxed for 8 h
3. 3
   TemperatureThe reaction was cooled to room temperature
4. 4
   Otherwas quenched with 1.6 mL of water, 1.6 mL of 15% NaOH
5. 5
   OtherThe solvent was removed in vacuo
6. 6
   FiltrationThe solution was filtered through celite
7. 7
   Otherthe solvent removed in vacuo

Procedure

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.

Source