Sodium hydride → 4-(2-oxo-2H-pyridin-1-yl)-benzaldehyde

HRID 1769663Notes

Reaction equation

HRID 1769663 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.F[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1>CN(C)C=O>[O:3]=[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]1[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 178516071HCID 178516071, compound

Product 1

HCID 107031494-(2-oxo-2H-pyridin-1-yl)-benzaldehydeYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4.4 g of 60% sodium hydride was suspended into 150 ml of N,N-dimethylformamide, to which 10.78 g of 2-hydroxypyridine was added little by little at a room temperature. 30 min after, 12.4 g of 4-fluorobenzaldehyde was added and stirred at 120° C. for 3 hours. The reaction solution was concentrated under a reduced pressure and iced water was added, which was extracted with chloroform. After drying with anhydrous magnesium sulfate, the solvent was distilled off. Resultant crystals were washed with ethyl acetate to obtain 10.3 g of the above-captioned compound as fine gray powder (yield: 52%).

Workup

  1. additionwas added little by little at a room temperature
  2. concentrationThe reaction solution was concentrated under a reduced pressure and iced water
  3. additionwas added
  4. extractionwhich was extracted with chloroform
  5. dry with materialAfter drying with anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. washResultant crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-a7bf9d35cc224ace91cdbff2fbb21931
Source dataset
uspto-grants-1995_01
Patent number
US05382595

Reaction notes

Loading…