Sodium hydride → 1-(4-Fluorobenzyl)-1h-pyridin-2-one

HRID 1360118Notes

Reaction equation

HRID 1360118 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1>CN(C=O)C>[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[O:3])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 178516071HCID 178516071, compound

Product 1

HCID 457961441-(4-Fluorobenzyl)-1h-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.61 g, 25 mmol) was added to a solution of 2-hydroxypyridine (2 g, 21 mmol) in DMF (20 mL) at 0 C. After stirring for 15 min, p-fluorobenzyl bromide (4.4 g, 2.9 mmol, 23 mmol) was added and the reaction mixture allowed to warm gradually to RT. The reaction mixture was quenched by addition of ice then poured into ether and extracted several times with ice water. The organic phase was then dried over Na2SO4, concentrated and the resulting yellow oil purified by normal phase Gilson chromatography eluting with 10% DCM, 70% Hexane, 20% EtOAc. 1-(4-Fluorobenzyl)pyridin-2(1H)-one was isolated as a white solid.

Workup

  1. customThe reaction mixture was quenched by addition of ice
  2. additionthen poured into ether
  3. extractionextracted several times with ice water
  4. dry with materialThe organic phase was then dried over Na2SO4
  5. concentrationconcentrated
  6. customthe resulting yellow oil purified by normal phase Gilson chromatography
  7. washeluting with 10% DCM, 70% Hexane, 20% EtOAc

Sources & evidence

ORD record
ord-ac1de632f1514864b91884afcfcec7e9
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

Loading…