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

HRID 339051Notes

Reaction equation

HRID 339051 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH3:16])=[N:13]2)=[CH:8][CH:7]=1.[O:17]1CCOCC1>O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH:16]=[O:17])=[N:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 709831307-(2-Methoxyethoxy)-2-methylquinoline

Product 1

HCID 867074817-(2-Methoxyethoxy)quinoline-2-carbaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 7-(2-methoxyethoxy)-2-methylquinoline (235 mg, 1.08 mmol) in dioxane (3 mL) and water (0.03 mL) was added SeO2 (132 mg, 1.19 mmol). The reaction mixture was heated at reflux for 2 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated under reduced pressure and The residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc) to give 7-(2-methoxyethoxy)quinoline-2-carbaldehyde (195 mg, 78%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe solid was removed by filtration
  4. washwashed with DCM
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-927d4340392144569c21981ad8497820
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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