Sodium Hydroxide → Quinolin-8-ylmethanol

HRID 1088785Notes

Reaction equation

HRID 1088785 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2)(=O)C.[OH-].[Na+]>CO>[OH:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 150531408-Quinolinemethanol,acetate(ester)

Product 1

HCID 594412Quinolin-8-ylmethanolYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-acetoxymethylquinoline (12.07 g) in methanol (80 ml) was added an 30% aqueous solution of sodium hydroxide, and the mixture was heated and refluxed for 1.5 hours. After distilling off the methanol, the resulting residue was extracted with chloroform. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The residue was recrystallized from ethyl acetate-n-hexane to give 8-hydroxymethylquinoline (9.21 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 1.5 hours
  3. distillationAfter distilling off the methanol
  4. extractionthe resulting residue was extracted with chloroform
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-954b08e55d2248718904bd63c0437371
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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