1-Bromopropane → HCID 15050203, compound

HRID 1587688Notes

Reaction equation

HRID 1587688 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[CH3:9][CH2:10][CH2:11]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1)[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 15050203HCID 15050203, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 16.5 g (0.15 mol) of 5-hydroxy-2-methylpyridine (commercially available), 18.8 g (0.15 mol) of n-propyl bromide and 8.00 g (0.06 mol) of anhydrous potassium carbonate with 100 ml of acetone was refluxed for 24 hours, the solvent was removed, 100 ml of water was added, and the mixture was extracted with chloroform. The chloroform layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under a reduced pressure. The residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:4) to give 9.63 g of an oily product (yield 42.1%).

Workup

  1. temperaturewas refluxed for 24 hours
  2. customthe solvent was removed
  3. addition100 ml of water was added
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-efeb8a4aba7f45a19c92a46d95cf52c3
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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