1-Bromooctane → 3-Pyridinecarboxylic acid, 6-(octyloxy)-

HRID 373460Notes

Reaction equation

HRID 373460 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[K+]>C(O)C>[CH2:11]([O:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 178418479HCID 178418479, compound

Product 1

HCID 35260273-Pyridinecarboxylic acid, 6-(octyloxy)-Yield 59.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Separately, 5 g of 6-hydroxypyridine-3-carboxylic acid and 10 g of n-octyl bromide were dissolved in 50 ml of ethanol, 50 ml of a 3N aqueous solution of potassium hydroxide was added to the solution, and the mixture was refluxed for 24 hours. Ethanol was removed from the reacted liquid by distillation, and the residue was neutralized with dilute hydrochloric acid and extracted with ethanol. The excess of n-octyl bromide was separated from the extract by the silica gel column chromatography using n-hexane as the developing solvent. Recrystallization from a mixed solvent of hexane and chloroform gave 5.4 g of 6-octyloxypyridine-3-carboxylic acid.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. customEthanol was removed from the reacted liquid by distillation
  3. extractionextracted with ethanol
  4. customThe excess of n-octyl bromide was separated from the
  5. extractionextract by the silica gel column chromatography
  6. customRecrystallization from a mixed solvent of hexane and chloroform

Sources & evidence

ORD record
ord-6444e81733094e2b818ee7498fbf536b
Source dataset
uspto-grants-1992_11
Patent number
US05164113

Reaction notes

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