Ethyl Bromide → 4-Bromo-1-ethylpyridin-2(1H)-one

HRID 919297Notes

Reaction equation

HRID 919297 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[CH:3]=1.Br[CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:10][CH3:11])[C:4](=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 178515446HCID 178515446, compound

Product 1

HCID 231159654-Bromo-1-ethylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-bromopyridin-2-ol (100 mg, 0.57 mmol), bromoethane (124 mg, 1.1 mmol) and potassium carbonate (238 mg, 1.7 mmol) in acetone (5 mL) was stirred at 60° C. for 3.0 h. The solution was allowed to cool to room temperature, filtered and the filter cake was washed with acetone (5 mL×2). The filtrate was collected and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography (PE:EA=20:1) to afford the title compound as a white solid LC/MS m/z=402.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.14 (d, 1 H), 6.81 (d, 1 H), 6.33 (dd, 1 H), 3.95 (q, 2 H), 1.34 (t, 3 H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washthe filter cake was washed with acetone (5 mL×2)
  4. customThe filtrate was collected
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified by silica gel column chromatography (PE:EA=20:1)

Sources & evidence

ORD record
ord-e6a17e750bbb418f960fda7ad82a2004
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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