Aluminium lithium hydride → 3-(Hydroxymethyl)pyridin-2(1H)-one

HRID 2400212Notes

Reaction equation

HRID 2400212 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11]>O1CCCC1>[OH:11][CH2:10][C:9]1[C:8](=[O:7])[NH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178418543HCID 178418543, compound

Product 1

HCID 106304823-(Hydroxymethyl)pyridin-2(1H)-oneYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. customreturned to room temperature
  2. temperaturebefore being refluxed for 8 h
  3. temperatureThe reaction was cooled to room temperature
  4. customwas quenched with 1.6 mL of water, 1.6 mL of 15% NaOH
  5. customThe solvent was removed in vacuo
  6. filtrationThe solution was filtered through celite
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-10dda8e7e6f34753b941450150cc9cb4
Source dataset
uspto-grants-2014_08
Patent number
US08795630B2

Reaction notes

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