Benzyl Bromide → HCID 23088640, compound

HRID 2091248Notes

Reaction equation

HRID 2091248 reaction equation
[C:1]([C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[Br:10]N1C(=O)CCC1=O.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C.C(#N)C.O>[CH2:18]([O:9][C:8]1[C:3]([C:1]#[N:2])=[N:4][C:5]([Br:10])=[CH:6][CH:7]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 1019203-Hydroxypyridine-2-carbonitrile

Product 1

HCID 23088640HCID 23088640, compoundYield 13%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-cyano-3-hydroxypyridine (10.0 g), water (40 mL) and acetonitrile (200 mL) was added N-bromosuccinimide (17.8 g) at 0° C., and the mixture was stirred at 0° C. for 2 hr, and at room temperature for 1 hr. Ethyl acetate was added to the reaction mixture. The solution was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a white solid. To a solution (200 mL) of the obtained solid in acetone were added benzyl bromide (11.9 mL) and potassium carbonate (23.1 g), and the mixture was stirred overnight with heating under reflux. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with methanol and toluene to give the title object compound (3.17 g, 13%) as a white solid.

Workup

  1. waitat room temperature for 1 hr
  2. washThe solution was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a white solid
  6. stirringthe mixture was stirred overnight
  7. temperaturewith heating
  8. temperatureunder reflux
  9. filtrationInsoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. washThe residue was washed with methanol and toluene

Sources & evidence

ORD record
ord-c52142ac4245485faa9be50f8acf71b7
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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