8-(Bromomethyl)quinoline → 8-Quinolinemethanol,acetate(ester)

HRID 1088784

Reaction equation

HRID 1088784 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.[C:13]([O-:16])(=[O:15])[CH3:14].[Na+]>CN(C)C=O>[C:13]([O:16][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 3469148-(Bromomethyl)quinolineHCID 517045Sodium Acetate

Product 1

HCID 150531408-Quinolinemethanol,acetate(ester)Yield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

8-Bromomethylquinoline (1.11 g) and sodium acetate (0.82 g) were suspended and dissolved in dimethyl formamide, and heated for 2 hours at 80° to 90° C. After completion of the reaction, dimethyl formamide was distilled off, and the residue was extracted with a mixed solvent of ethyl acetate-toluene (3:1). The solvent was distilled off to give 8-acetoxymethylquinoline (0.86 g).

Workup

  1. temperatureheated for 2 hours at 80° to 90° C
  2. distillationwas distilled off
  3. extractionthe residue was extracted with a mixed solvent of ethyl acetate-toluene (3:1)
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-d22eefa4c1ef4d9eb230b06c54d466d0
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Linked notes

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