Benzyl Bromide → 1-benzyl-4-(benzyloxy)pyridin-2(1H)-one

HRID 2243564Notes

Reaction equation

HRID 2243564 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH2:16]([N:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]1=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 101930321-benzyl-4-(benzyloxy)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolvent

Procedure

In following a method similar to that described in Katigiri, N; Sato, M.; Yoneda, N.; Saikawa, S.; Sakamoto, T.; Muto, M.; Kaneko, C. J. Chem. Soc. Perkin Trans. 1, 1289-1296, 1986, a solution of 4-benzyloxy-2-pyridone 1 (1.00 g, 5.00 mmol), benzylbromide (4.28 g, 2.97 mL, 25.0 mmol), finely powdered sodium hydroxide (1.00 g, 25.0 mmol), and tetrabutylammonium hydrogen sulfate (0.679 g, 2.00 mmol) in benzene (180 mL) was heated at reflux for 2 h and then cooled to room temperature. The reaction mixture was concentrated and the residue was partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown solid. This solid was recrystallized from ethyl acetate to afford 1-benzyl-4-benzyloxy-2-pyridone 2 as a tan solid. MS (MH+) 292.2; Calculated 291 for C19H17NO2.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between dichloromethane and water
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane
  6. washThe combined organic phases were washed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a brown solid
  11. customThis solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4e831c1bccb84a8c830cc02ee7b9e1e7
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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