Benzyl Bromide → HCID 71139868, compound

HRID 539514Notes

Reaction equation

HRID 539514 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.O.C(Cl)(Cl)Cl>[CH2:16]([N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]1=[O:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 887313-Methoxy-2-pyridone

Product 1

HCID 71139868HCID 71139868, compoundYield 75.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring reaction mixture of 3-methoxypyridine-2-one (0.2 g, 1.6 mmol) and K2CO3 (0.66 g, 4.8 mmol) in DMF (8 mL) was added benzyl bromide (0.33 g, 1.92 mmol) dropwise in a condenser equipped round bottom flask. Reaction mixture was then heated to 100° C. After overnight stirring, reaction mixture was cooled down and diluted with water (40 mL) and CHCl3 (50 mL). Organic layer was washed with water (3×40 mL), brine (1×30 mL) and dried over Na2SO4 and solvent was evaporated in vacuo to yield pure 141b (0.26 g, 75%) as a colorless oil without any further purification needed. 1H NMR (400 MHz, CDCl3) δ 7.26 (m, 5H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 6.54 (dd, J=7.5, 1.6 Hz, 1H), 6.03 (m, 1H), 5.13 (s, 2H), 3.76 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 157.94, 150.05, 136.31, 128.56, 128.01, 127.74, 127.70, 111.82, 104.83, 104.81, 55.64, 51.64.

Workup

  1. customequipped round bottom flask
  2. customReaction mixture
  3. customreaction mixture
  4. temperaturewas cooled down
  5. washOrganic layer was washed with water (3×40 mL), brine (1×30 mL)
  6. dry with materialdried over Na2SO4 and solvent
  7. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-b98b439ec6ee4165b61e82f15d2dd866
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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