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

HRID 336122Notes

Reaction equation

HRID 336122 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:9]([O:8][N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]1=[O:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178526252HCID 178526252, compound

Product 1

HCID 8247291-(benzyloxy)pyridin-2(1H)-oneYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-hydroxypyridine-1-oxide (0.50 g, 4.5 mmol) was reacted with benzyl bromide (0.64 mL, 5.4 mmol) in DMF (10 mL) in the presence of K2CO3 (1.8 g, 13.5 mmol) at 80° C. for 16 h. After cooling to room temperature, the solvent was removed by rotary evaporation. The crude product was redissolved in DCM and washed twice with water. The organic layer was then dried over MgSO4, filtered, and concentrated resulting in 7 as a white solid in 84% yield (0.78 g, 3.8 mmol) without the need for further purification. 1H NMR (400 MHz, CDCl3) δ=7.41-7.36 (m, 5H), 7.25 (td, J1=6.8 Hz, J2=2.0 Hz, 1H), 7.10 (dd, J1=7.2 Hz, J2=2.0 Hz, 1H), 6.68 (dd, J1=9.2 Hz, J2=1.6 Hz, 1H), 5.91 (td, J1=6.8 Hz, J2=1.6 Hz, 1H), 5.28 (s, 2H). 13C NMR (100 MHz, CDCl3) δ=159.2, 138.9, 136.9, 133.9, 130.3, 129.6, 128.9, 122.9, 104.7, 78.6. ESI-MS(+): m/z 202.19 [M+H]+, 224.29 [M+Na]+.

Workup

  1. customthe solvent was removed by rotary evaporation
  2. dissolutionThe crude product was redissolved in DCM
  3. washwashed twice with water
  4. dry with materialThe organic layer was then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f90204c4e410452489abec9a5bff64c0
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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