1,4-Dioxane → 7-(2-Hydroxyethyl)quinoline-2-carbaldehyde

HRID 339082Notes

Reaction equation

HRID 339082 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][CH2:13][OH:14])=[CH:7][CH:8]=2)[N:3]=1.[O:15]1CCOCC1>O>[OH:14][CH2:13][CH2:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH:1]=[O:15])=[N:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 86707554HCID 86707554, compound

Product 1

HCID 867075557-(2-Hydroxyethyl)quinoline-2-carbaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-methylquinolin-7-yl)ethanol (0.220 g, 1.17 mmol) was dissolved in dioxane (5 mL) and water (0.05 mL). The reaction was treated with SeO2 (0.156 g, 1.41 mmol) and the mixture was heated to reflux for 2 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes 5:1) to give 7-(2-hydroxyethyl)quinoline-2-carbaldehyde (0.21 g, 1.04 mmol, 89% yield) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customthe solid was removed by filtration
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes 5:1)

Sources & evidence

ORD record
ord-fa410f2bf75e4e12b55027bda56be480
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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