1-Bromohexane → HCID 19756117, compound

HRID 1587686Notes

Reaction equation

HRID 1587686 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:11]([O:1][C:2]1[C:3]([C:8]([O:10][CH2:8][CH2:3][CH2:2][CH2:7][CH2:6][CH3:5])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 134013-Hydroxypicolinic Acid

Product 1

HCID 19756117HCID 19756117, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2.80 g (20 mmol) of 3-hydroxypicolinic acid, 4.13 g (25 mmol) of n-hexyl bromide and 30 ml of N,N,-dimethylformamide was added 2.8 g (0.02 mmol) of anhydrous potassium carbonate, and the mixture was stirred under heating at 100° C. for 4.5 hours. After cooling, 60 ml of ice-water was added, and the mixture extracted with ethyl acetate. The solution was subjected to evaporation under a reduced pressure and the residue separated by silica gel column chromatography (ethyl acetate:hexane=3:7), to obtain 2.60 g of a colorless oily substance (yield 40.5%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture extracted with ethyl acetate
  3. customThe solution was subjected to evaporation under a reduced pressure
  4. customthe residue separated by silica gel column chromatography (ethyl acetate:hexane=3:7)
  5. customto obtain 2.60 g of a colorless oily substance (yield 40.5%)

Sources & evidence

ORD record
ord-66d0756d31f54abdbc488253e58f8fc2
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

Loading…